HCID 67355362, compound → HCID 67356194, compound

HRID 627385Notes

Reaction equation

HRID 627385 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[N:14]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:26]([O:30][C:31]([N:33]1[CH:38]2[CH2:39][CH2:40][CH:34]1[CH2:35][N:36]([C:41]([C:43]1[CH:44]=[N:45][C:46]([NH2:49])=[CH:47][CH:48]=1)=[O:42])[CH2:37]2)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31]([N:33]1[CH:34]2[CH2:40][CH2:39][CH:38]1[CH2:37][N:36]([C:41]([C:43]1[CH:44]=[N:45][C:46]([NH:49][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3](=[O:4])[N:2]([CH3:25])[CH3:1])[N:14]([CH:15]5[CH2:20][CH2:19][N:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:17][CH2:16]5)[C:8]=4[N:9]=3)=[CH:47][CH:48]=1)=[O:42])[CH2:35]2)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 67355362HCID 67355362, compoundHCID 89629725HCID 89629725, compound

Product 1

HCID 67356194HCID 67356194, compoundYield 49.1%

Procedure

Following general N—C coupling procedure 1, 1, 7-(1-tert-Butyl-piperidin-4-yl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (90 mg, 0.247 mmol, 1.0 eq) was combined with 3-(6-Amino-pyridine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (90 mg, 0.272 mmol, 1.1 eq) which gave 3-{6-[7-(1-tert-Butyl-piperidin-4-yl)-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-pyridine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (80 mg) in 47% yield. MS m/z 660.3 (M+H)+.

Sources & evidence

ORD record
ord-51cb6a577ae847519180e4278d72b461
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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