tert-Butyl azepan-3-ylcarbamate → HCID 71253713, compound

HRID 1775038Notes

Reaction equation

HRID 1775038 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.[NH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]([NH:36]C(=O)OC(C)(C)C)[CH2:30]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:29]5[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]([NH2:36])[CH2:30]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 20745759tert-Butyl azepan-3-ylcarbamateHCID 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 71253713HCID 71253713, compoundYield 58.6%

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 azepan-3-ylcarbamate were reacted. The product was deprotected to give 226 as a white solid (58.6% over two steps). 1H NMR (400 MHz, DMSO) δ 9.04 (s, 1H), 8.52 (s, 1H), 8.32 (s, 1H), 8.28 (s, 1H), 7.94 (s, 1H), 7.64 (t, J=7.9 Hz, 1H), 7.43 (d, J=7.4 Hz, 1H), 6.75 (d, J=8.5 Hz, 1H), 4.18 (d, J=12 Hz, 1H), 4.13-4.06 (m, 1H), 3.90 (s, 3H), 3.54 (m, 1H), 3.36 (d, J=8.8 Hz, 1H), 3.32 (s, 1H), 2.05-1.95 (m, 1H), 1.84-1.69 (m, 3H), 1.53-1.41 (m, 1H), 1.40-1.27 (m, 1H); 2 protons not seen. LC/MS: m/z 389.2 [M+1]

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6308e7c3a5814b719548afcba26a4ae5
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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