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

HRID 79202

Reaction equation

HRID 79202 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]([CH2:34][N:35]2[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]2)=[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]([CH2:34][N:35]5[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]5)=[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 45788993tert-Butyl 4-((6-chloropyridin-3-yl)methyl)piperazine-1-carboxylateHCID 582995859-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 441329039-cyclopentyl-N-(5-(1-piperazinylmethyl)-2-pyridinyl)-9 H-pyrido[4',3':4,5]-pyrrolo[2,3-d]pyrimidin-2-amine

Procedure

Compound 338 was prepared as an off-white solid (TFA salt) from compound 4 and compound 339 using chemistry similar to that described in example 200. 1H NMR (500 MHz, CD3OD) δ ppm 9.68 (1 H, s), 9.35 (1 H, s), 8.68 (2 H, q, J=6.3 Hz), 8.43 (1 H, d, J=1.5 Hz), 8.26 (1 H, dd, J=8.9, 2.1 Hz), 7.88 (1 H, d, J=8.8 Hz), 5.48 (1 H, quin, J=8.7 Hz), 3.78 (2 H, s), 3.27-3.30 (4 H, m), 2.83 (4 H, br. s.), 2.48-2.59 (2 H, m), 2.15-2.31 (4 H, m), 1.83-1.97 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 429.2.

Sources & evidence

ORD record
ord-f0bcf7d094b1467c8629eda6027474fd
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Linked notes

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