HCID 67355622, compound → HCID 67354482, compound

HRID 1850552Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][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:20]([O:24][C:25]([N:27]1[CH2:32][C@@H:31]2[CH2:33][C@H:28]1[CH2:29][N:30]2[C:34]([C:36]1[CH:37]=[N:38][C:39]([NH2:42])=[CH:40][CH:41]=1)=[O:35])=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25]([N:27]1[CH2:32][C@@H:31]2[CH2:33][C@H:28]1[CH2:29][N:30]2[C:34]([C:36]1[CH:37]=[N:38][C:39]([NH:42][C:10]2[N:11]=[CH:12][C:7]3[CH:6]=[C:5]([C:3](=[O:4])[NH:2][CH3:1])[N:14]([CH:15]4[CH2:19][CH2:18][CH2:17][CH2:16]4)[C:8]=3[N:9]=2)=[CH:40][CH:41]=1)=[O:35])=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

Reactant 2

HCID 67355622HCID 67355622, compound

HCID 866410801211444-14-2

Product 1

HCID 67354482HCID 67354482, compound

Procedure

Following general N—C coupling procedure 1, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methylamide, see WO 2010020675, (0.120 g, 0.431 mmol) was combined with (1S,4S)-5-(6-amino-pyridine-3-carbonyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.144 g, 0.452 g, 1.05 eq), which gave (1S,4S)-5-[6-(7-Cyclopentyl-6-methylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester as a yellow solid. This material was used directly in the following step 3. MS m/z 561.5 (M+H)+.

Sources & evidence

ORD record: ord-e97c8215cdc14cea878528364a9cb7c7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957074B2

Reaction notes

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