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Triethylamine → 3-Amino-6-[4-[[[(1S)-2-methoxy-1-methylethyl]amino]carbonyl]phenyl]-N-3-pyridinyl-2-pyrazinecarboxamide hydrochloride

HRID 736613
Notes
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Reaction equation

HRID 736613 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)=[N:13][C:14]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:16].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.[CH3:65][O:66][CH2:67][C@@H:68]([NH2:70])[CH3:69].C(Cl)[Cl:72].CO>>[ClH:72].[NH2:8][C:9]1[C:14]([C:15]([NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:16])=[N:13][C:12]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:70][C@@H:68]([CH3:69])[CH2:67][O:66][CH3:65])=[O:30])=[CH:26][CH:25]=2)=[CH:11][N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70215362-Propanamine, 1-methoxy-, (2S)-HCID 102686064-(5-Amino-6-[(pyridin-3-ylamino)carbonyl]pyrazin-2-yl]benzoic acidHCID 21226129Dichloromethane methanol

Product 1

HCID 100720733-Amino-6-[4-[[[(1S)-2-methoxy-1-methylethyl]amino]carbonyl]phenyl]-N-3-pyridinyl-2-pyrazinecarboxamide hydrochlorideYield 29%

Procedure

Triethylamine (0.12 mL, 0.89 mmol) was added to a mixture of 4-{5-amino-6-[(pyridin-3-ylamino)carbonyl]pyrazin-2-yl}benzoic acid (100 mg, 0.30 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.105 g, 0.33 mmol) and 1-hydroxybenzotriazole (44 mg, 0.33 mmol) in methylene chloride/methanol (9:1, 10 mL) at room temperature. (S)-(+)-1-methoxy-2-propylamine was added dropwise and the resulting mixture was stirred at room temperature for 1.5 h. The mixture was evaporated onto silica and purified by chromatography on silica using toluene/acetonitrile, (2:1 to 0:1) as the eluent. The formed yellow solid was dissolved in methylene chloride. Hydrochloride acid in diethyl ether (0.4 mL, 1 M) was added and the mixture was stirred at room temperature. The precipitated product was filtrated off and dried in vacuo at 40° C. giving 39 mg (29% yield) of the product as a yellow solid. 1H NMR (DMSO-d6) δ 9.38 (m, 1H), 9.08 (s, 1H), 8.85 (d, J=9 Hz, 1H), 8.67 (d, J=5 Hz, 1H), 8.36 (d, J=8 Hz, 2H), 8.32 (d, J=8 Hz, 2H), 8.03 (m, J=6 Hz, 1H), 7.99 (d, J=8 Hz, 2H), 7.80 (br s, 1H), 4.23 (m, 1H), 3.45 (m, 1H), 3.32 (m, 1H), 3.29 (s, 3H), 1.17 (d, J=7 Hz, 3H); 13C NMR (D2O) δ 165.8, 165.5, 154.9, 146.3, 138.2, 138.1, 137.5, 135.6, 134.3, 128.0, 126.9, 125.6, 123.0, 75.3, 58.4, 44.8, 17.6; MS (ESP) m/z 407 (M++1).

Workup

  1. customThe mixture was evaporated onto silica
  2. custompurified by chromatography on silica
  3. dissolutionThe formed yellow solid was dissolved in methylene chloride. Hydrochloride acid in diethyl ether (0.4 mL, 1 M)
  4. additionwas added
  5. stirringthe mixture was stirred at room temperature
  6. filtrationThe precipitated product was filtrated off
  7. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-01a2a1aacedd44ae882bf6b7e65dd8cc
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07595319B2

Reaction notes

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