N-(tert-butoxycarbonyl)glycine → HCID 58315463, compound

HRID 1483081Notes

Reaction equation

[CH3:1][N:2]([CH3:33])[C:3]([C:5]1[N:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].C(OC([NH:41][CH2:42][C:43](O)=[O:44])=O)(C)(C)C>>[CH3:1][N:2]([CH3:33])[C:3]([C:5]1[N:27]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][N:24]([C:43](=[O:44])[CH2:42][NH2:41])[CH2:23][CH2:22]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycine

HCID 58315424HCID 58315424, compound

Product 1

HCID 58315463HCID 58315463, compoundYield 71.4%

Procedure

By repeating procedures outlined in Example 12, 7-cyclopentyl-2-(5-piperazin-1-ylmethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (0.108 g, 0.241 mmol) and tert-butoxycarbonylamino-acetic acid (42 mg, 0.241 mmol) gave 2-{5-[4-(2-amino-acetyl)-piperazin-1-ylmethyl]-pyridin-2-ylamino}-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a white solid (87 mg, 69%). MS (ESI) m/z 506.3 (M+H)+ (method B).

Sources & evidence

ORD record: ord-b2c3852ad43e47a88bdb863c0def110c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416136B2

Reaction notes

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