tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate → Ribociclib Impurity 2(N-desmethyl Ribociclib)

HRID 1483142Notes

Reaction equation

HRID 1483142 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(OC([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[N:35][C:36]([NH2:39])=[CH:37][CH:38]=2)[CH2:29][CH2:28]1)=O)(C)(C)C>>[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]([NH:39][C:36]3[CH:37]=[CH:38][C:33]([N:30]4[CH2:29][CH2:28][NH:27][CH2:32][CH2:31]4)=[CH:34][N:35]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 866410801211444-14-2

Product 1

HCID 44818949Ribociclib Impurity 2(N-desmethyl Ribociclib)Yield 77%

Procedure

Following Buchwald Method B, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methylamide (500 mg, 1.80 mmol) and 4-(6-amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (550 mg, 1.98 mmol) gave 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methylamide (580 mg, 77%). MS (ESI) m/z 421.2 (M+H)|

Sources & evidence

ORD record
ord-7f00296d42f8410cad78a319b6339c88
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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