Diisopropylethylamine → 3-{1-[6-(5-Benzyloxy-pyrrolo[3,2-b]pyridine-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74613Notes

Reaction equation

HRID 74613 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.[CH2:21]([O:28][C:29]1[N:34]=[C:33]2[CH:35]=[CH:36][N:37]([C:38]([C:40]3[CH:45]=[C:44](Cl)[N:43]=[CH:42][N:41]=3)=[O:39])[C:32]2=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:21]([O:28][C:29]1[N:34]=[C:33]2[CH:35]=[CH:36][N:37]([C:38]([C:40]3[N:41]=[CH:42][N:43]=[C:44]([N:17]4[CH2:18][CH2:19][CH:14]([N:10]5[CH2:9][CH2:8][C:7]6[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=6[NH:12][C:11]5=[O:13])[CH2:15][CH2:16]4)[CH:45]=3)=[O:39])[C:32]2=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 58386717HCID 58386717, compound

Product 1

HCID 583865993-{1-[6-(5-Benzyloxy-pyrrolo[3,2-b]pyridine-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.11 g (0.40 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 0.14 g (0.38 mmol) (5-benzyloxy-pyrrolo[3,2-b]pyridin-1-yl)-(6-chloro-pyrimidin-4-yl)-methanone and 0.10 mL (0.58 mmol) DIPEA in 5 mL DMF were stirred overnight at RT. The reaction mixture was diluted with water and stirred for 30 min. The precipitate formed was suction filtered, washed with water and MeOH and dried.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water and MeOH
  4. customdried

Sources & evidence

ORD record
ord-14ad3ae1b02144a5941e915b6e34550d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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