Diisopropylethylamine → 4,4-dimethyl-7-({2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1815207Notes

Reaction equation

HRID 1815207 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21]([C:23]3[C:24](F)=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:30][CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[N:38](C(=O)C)[CH:39]=[CH:40][C:33]=12.CCN(C(C)C)C(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21]([C:23]3[C:24]([NH:30][CH2:31][C:32]4[CH:37]=[CH:36][N:35]=[C:34]5[NH:38][CH:39]=[CH:40][C:33]=45)=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 219595167-[(2-fluoro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 219614331-(4-(Aminomethyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)ethanone

Product 1

HCID 600537294,4-dimethyl-7-({2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Procedure

A mixture of 7-[(2-fluoro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.24 g), 1-(4-aminomethyl-pyrrolo[2,3-b]pyridin-1-yl)-ethanone (0.14 g), DIEA (0.8 mL) and IpOH (0.8 mL) was subjected to a MicroWave condition (170° C., 1000 s) twice. Evaporation of solvent yielded the crude compound, which was purified by chromatography through silica gel (15 g, 5% MeOH/CH2Cl2) to afford 4,4-dimethyl-7-({2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester.

Workup

  1. customwas subjected to a MicroWave condition (170° C., 1000 s)
  2. customEvaporation of solvent
  3. customyielded the crude compound, which
  4. customwas purified by chromatography through silica gel (15 g, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-795a71391b994fdcbc8ef137edf7c98f
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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