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Diisopropylethylamine → HCID 70817143, compound

HRID 82125
Notes
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Reaction equation

HRID 82125 reaction equation
Cl.[N:2]1[C:11]2[CH2:10][N:9]([CH2:12][C:13]([OH:15])=O)[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]([C:23]([C:25]2[C:33]3[CH:32]=[N:31][CH:30]=[N:29][C:28]=3[N:27]([CH:34]([CH3:36])[CH3:35])[CH:26]=2)=[O:24])[CH:20]=[N:21][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(OCC)(=O)C.CN(C=O)C>[N:2]1[C:11]2[CH2:10][N:9]([CH2:12][C:13]([NH:16][C:17]3[CH:22]=[N:21][CH:20]=[C:19]([C:23]([C:25]4[C:33]5[CH:32]=[N:31][CH:30]=[N:29][C:28]=5[N:27]([CH:34]([CH3:36])[CH3:35])[CH:26]=4)=[O:24])[CH:18]=3)=[O:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70817456(5-aminopyridin-3-yl)(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanoneHCID 70817716(5,8-Dihydro-6H-[1,7]naphthyridin-7-yl)-acetic acid hydrochloride

Product 1

HCID 70817143
HCID 70817143, compound
Yield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a DMF solution of (5,8-Dihydro-6H-[1,7]naphthyridin-7-yl)-acetic acid hydrochloride (Preparation 235) (34.2 mg, 0.18 mmol) were added (5-Amino-pyridin-3-yl)-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (Preparation 95) (50 mg, 0.18 mmol), HATU (136.4 mg, 0.36 mmol) and Hunig's base (0.092 ml, 0.54 mmol). The mixture was heated at 50° C. for 20 hours and then diluted with ethyl acetate, washed with water, brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude solid was purified over preparative TLC eluting with 5% MeOH/EtOAc to afford the title compound as off white solid in 26% yield, 21 mg. 1H NMR (400 MHz, DMSO-D6) δ: 1.55 (d, 6H), 2.85-2.92 (m, 4H), 3.45 (s, 2H), 3.80 (s, 2H), 5.10 (m, 1H), 7.19 (dd, 1H), 7.56 (d, 1H), 8.32 (d, 1H), 8.53 (s, 1H), 8.56 (t, 1H), 8.73 (d, 1H), 8.99 (s, 1H), 9.07 (d, 1H), 9.45 (s, 1H), 10.31 (s, 1H); LCMS (system 9): Rt=1.77 min; m/z 456 [M+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness in vacuo
  4. customThe crude solid was purified over preparative TLC
  5. washeluting with 5% MeOH/EtOAc

Sources & evidence

ORD record
ord-46a158f66223483983842b65f408510a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846698B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes