HCID 71253878, compound → HCID 86676690, compound

HRID 1775034Notes

Reaction equation

HRID 1775034 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]3)[CH:12]=[CH:13][CH:14]=2)O1.Cl[C:31]1[C:39]2[C:34](=[CH:35][N:36]=[C:37]([C:40]3[CH:41]=[N:42][N:43]([CH3:45])[CH:44]=3)[CH:38]=2)[N:33]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)[N:32]=1>>[CH3:45][N:43]1[CH:44]=[C:40]([C:37]2[CH:38]=[C:39]3[C:31]([C:9]4[CH:10]=[C:11]([N:15]5[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:16]5)[CH:12]=[CH:13][CH:14]=4)=[N:32][N:33]([CH:46]4[CH2:51][CH2:50][CH2:49][CH2:48][O:47]4)[C:34]3=[CH:35][N:36]=2)[CH:41]=[N:42]1

Participants

3

Reactant 2

HCID 71253878HCID 71253878, compoundHCID 71254297HCID 71254297, compound

Product 1

HCID 86676690HCID 86676690, compoundYield 60%

Procedure

Following the Suzuki coupling procedure in Example 172, (R)-tert-butyl 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-3-ylcarbamate and 3-chloro-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine were reacted to give tert-butyl (3R)-1-(3-(5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazo-lo[3,4-c]pyridin-3-yl)phenyl)piperidin-3-ylcarbamate as a solid (60%). 1H NMR (400 MHz, CDCl3) δ 9.12 (s, 1H), 7.97 (s, 1H), 7.95 (s, 1H), 7.93 (s, 1H), 7.34 (t, J=7.8 Hz, 1H), 7.26 (s, 1H), 7.19 (s, 1H), 6.73 (d, J=8.4 Hz, 1H), 5.90-5.83 (m, 1H), 4.09-4.00 (m, 2H), 3.97 (s, 3H), 3.88-3.76 (m, 2H), 3.67 (s, 1H), 3.52 (s, 1H), 3.17 (s, 1H), 3.03 (s, 1H), 2.64-2.52 (m, 1H), 2.17 (d, J=10.1 Hz, 2H), 2.09-1.99 (m, 1H), 1.84-1.70 (m, 5H), 1.65-1.54 (m, 1H), 1.41 (s, 9H). LC/MS: m/z 558.2 [M+1].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-94949f0b820c4bf4aa9fffbc99982468
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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