tert-Butyl [3-(trifluoromethyl)pyrrolidin-3-yl]carbamate → HCID 71253982, compound

HRID 1775086Notes

Reaction equation

HRID 1775086 reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:45])([F:44])[C:31]1([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][NH:33][CH2:32]1>>[CH3:22][N:20]1[CH:21]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[N:7]=[C:2]([N:33]5[CH2:34][CH2:35][C:31]([C:30]([F:45])([F:44])[F:29])([NH2:36])[CH2:32]5)[CH:3]=[CH:4][CH:5]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=[N:19]1

Participants

3

Reactant 2

HCID 19691491tert-Butyl [3-(trifluoromethyl)pyrrolidin-3-yl]carbamateHCID 712534393-(6-fluoropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71253982HCID 71253982, compoundYield 47.3%

Procedure

Following the procedures as described in Example 189, 3-(6-fluoropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and tert-butyl 3-(trifluoromethyl)pyrrolidin-3-ylcarbamate were reacted. The product was deprotected and purified to give 286 as a white solid (47.3% over two steps). 1H NMR (400 MHz, DMSO) δ 9.02 (s, 1H), 8.65 (s, 1H), 8.09 (s, 1H), 7.86 (s, 1H), 7.65 (t, J=7.9 Hz, 1H), 7.44 (d, J=7.4 Hz, 1H), 6.51 (d, J=8.3 Hz, 1H), 3.91-3.86 (m, 4H), 3.84-3.65 (m, 3H), 2.47 (s, 2H), 2.38-2.27 (m, 1H), 2.05 (dd, J=12.3, 6.1 Hz, 1H); 1 proton not seen. LC/MS: m/z 429.2 [M+1]

Workup

  1. customwere reacted
  2. custompurified

Sources & evidence

ORD record
ord-ad5fea5391864a8e9ef082f96202f1af
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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