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Diisopropylethylamine → 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide

HRID 1255860
Notes
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Reaction equation

HRID 1255860 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([OH:24])=O)[S:20][CH:21]=3)[CH:13]=2)[CH:3]=1.[F:25][C:26]([F:37])([F:36])[CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=1)[NH2:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([NH:28][CH:27]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=4)[C:26]([F:25])([F:36])[F:37])=[O:24])[S:20][CH:21]=3)[CH:13]=2)[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 649850182,2,2-Trifluoro-1-(6-methyl-pyridin-2-YL)-ethylamineHCID 687770504-(6-Pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)thiophene-2-carboxylic acid hydrochloride

Product 1

HCID 68775719
4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)thiophene-2-carboxylic acid hydrochloride (20 mg, 0.06 mmol), 2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethanamine (step C, 12 mg, 0.06 mmol), BOP (41 mg, 0.09 mmol) and N,N-diisopropylethylamine (16 □L, 0.09 mmol) in DMF (0.6 mL) was stirred at 40° C. for 4 hours. The reaction was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated in vacuo. Purification by reverse phase LC gave 4-(6-pyridin-3-ylpyrazolo[1,5-a]pyrimidin-3-yl)-N-[2,2,2-trifluoro-1-(6-methylpyridin-2-yl)ethyl]thiophene-2-carboxamide. 1H NMR (600 MHz, CDCl3): δ 9.42 (bs, 1H), 9.11 (s, 1H), 9.00 (d, J=2.4 Hz, 1H), 8.84 (d, J=5.3 Hz, 1H), 8.81 (d, J=2.3 Hz, 1H), 8.55 (s, 2H), 8.34 (d, J=8.3 Hz, 1H), 8.17 (s, 1H), 7.99 (t, J=8.5 Hz, 1H), 7.85 (dd, J=7.9, 5.3 Hz, 1H), 7.58 (d, J=7.4 Hz, 1H), 7.48 (m, 1H), 6.13 (m, 1H), 3.48 (s, 3H). LC-MS EIMS: m/z 495.1 [M+H]+.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by reverse phase LC

Sources & evidence

ORD record
ord-f408713b961f48d7979aa1eb516fe821
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461162B2

Reaction notes

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