Trifluoroacetic acid → 9-Cyclopentyl-N-(5-(1-piperazinylsulfonyl)-2-pyridinyl)-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 876040Notes

Reaction equation

HRID 876040 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([N:13]2[C:17]3[N:18]=[C:19]([NH2:22])[N:20]=[CH:21][C:16]=3[C:15]3[CH:23]=[CH:24][N:25]=[CH:26][C:14]2=3)[CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[C:28]1[N:33]=[CH:32][C:31]([S:34]([N:37]2[CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1>>[CH:8]1([N:13]2[C:17]3[N:18]=[C:19]([NH:22][C:28]4[CH:29]=[CH:30][C:31]([S:34]([N:37]5[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]5)(=[O:36])=[O:35])=[CH:32][N:33]=4)[N:20]=[CH:21][C:16]=3[C:15]3[CH:23]=[CH:24][N:25]=[CH:26][C:14]2=3)[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11739940Tert-butyl 4-(6-chloropyridin-3-ylsulfonyl)piperazine-1-carboxylateHCID 582995859-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 582999149-Cyclopentyl-N-(5-(1-piperazinylsulfonyl)-2-pyridinyl)-9H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

Procedure

Compound 359 was prepared as a white solid (TFA salt) from compound 4 and compound 360 using chemistry similar to that described in example 200. 1H NMR (500 MHz, CD3OD) δ ppm 9.59 (1 H, s), 9.29 (1 H, s), 8.72-8.78 (2 H, m), 8.63-8.66 (1 H, m), 8.61 (1 H, d), 8.22 (1 H, dd, J=8.8, 2.4 Hz), 5.51 (1 H, quin, J=8.9 Hz), 3.37 (8 H, s), 2.46-2.60 (2 H, m), 2.13-2.34 (4 H, m), 1.87-2.01 (2 H, m). LCMS-ESI (POS), M/Z, M+1. Found 478.9.

Sources & evidence

ORD record
ord-9ae47a4f14b9434594d6304ea0d88dad
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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