Hydrochloric Acid → HCID 68458635, compound

HRID 2387491Notes

Reaction equation

N1CCNCC1.[CH:7]12[CH2:39][CH:10]([N:11]([CH2:13][CH2:14][N:15]3[C:23]4[C:18](=[CH:19][C:20]([N:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)=[CH:26][C:25]5=[O:38])=[CH:21][CH:22]=4)[CH:17]=[N:16]3)[CH2:12]1)[CH2:9][O:8]2.[ClH:40]>>[ClH:40].[C@H:7]12[CH2:39][C@H:10]([N:11]([CH2:13][CH2:14][N:15]3[C:23]4[C:18](=[CH:19][C:20]([N:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=6)=[CH:26][C:25]5=[O:38])=[CH:21][CH:22]=4)[CH:17]=[N:16]3)[CH2:12]1)[CH2:9][O:8]2

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 4837Piperazine

HCID 25054550HCID 25054550, compound

Product 1

HCID 68458635HCID 68458635, compoundYield 18%

Procedure

Following the procedure of Example 27 (step b), but substituting 2-oxa-5-azabicyclo[2.2.1]heptane for piperazine, 1-(1-(2-(2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl)ethyl)-1H-indazol-5-yl)-4-(benzyloxy)pyridin-2(1H)-one was prepared as a yellow powder: 1H NMR (500 MHz, DMSO-d6) δ 8.02 (s, 1H), 7.66 (d, J=1.6 Hz, 1H), 7.51 (d, J=8.9 Hz, 1H), 7.44-7.35 (m, 6H), 7.29 (d, J=7.4 Hz, 1H), 6.10-6.05 (m, 2H), 5.06 (s, 2H), 4.48 (t, J=6.9 Hz, 2H), 4.36 (s, 1H), 3.95 (d, J=7.8 Hz, 1H), 3.59 (dd, J=7.6, 1.7 Hz, 1H), 3.40 (s, 1H), 3.15-3.05 (m, 1H), 2.88 (dd, J=9.9, 1.6 Hz, 1H) 2.53 (d, J=9.8 Hz, 1H), 1.80-1.74 (m, 2H), 1.72-1.67 (m, 1H); ESI MS m/z 443 [M+H]+This was converted to the HCl salt to give the title compound (17.4 mg, 18%) as a yellow powder: ESI MS m/z 443 [M+H]+.

Workup

customwas prepared as a yellow powder

Sources & evidence

ORD record: ord-77571f5f9d894505b07887827b68a2fb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268868B2

Reaction notes

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