Hydrochloric Acid → HCID 131729460, compound

HRID 2370313Notes

Reaction equation

CN1C2C=CC=C(C([O-])=O)C=2C(CN[C@H]2C3CCN(CC3)C2)=N1.[Li+].[CH3:25][N:26]1[C:30]2[CH:31]=[N:32][CH:33]=[C:34]3[C:35](=[O:46])[C@H:36]([CH:38]4[CH:43]5[CH2:44][CH2:45][N:40]([CH2:41][CH2:42]5)[CH2:39]4)[CH2:37][C:28]([C:29]=23)=[N:27]1.[ClH:47]>>[ClH:47].[CH3:25][N:26]1[C:30]2[CH:31]=[N:32][CH:33]=[C:34]3[C:35](=[O:46])[C@H:36]([CH:38]4[CH:43]5[CH2:42][CH2:41][N:40]([CH2:45][CH2:44]5)[CH2:39]4)[CH2:37][C:28]([C:29]=23)=[N:27]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 66772564HCID 66772564, compound

HCID 66772595HCID 66772595, compound

Product 1

HCID 131729460HCID 131729460, compoundYield 83%

Procedure

Following general procedure CP-H, lithium (S)-1-methyl-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate was converted to (S)-2-methyl-7-(quinuclidin-3-yl)-7,8-dihydropyrazolo[3,4,5-de]isoquinolin-6(2H)-one, which was immediately and treated with hydrochloric acid following general procedure GP-I to give (S)-2-methyl-7-(quinuclidin-3-yl)-7,8-dihydropyrazolo[3,4,5-de]isoquinolin-6(2H)-one, hydrochloride salt (40 mg, 83%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.01 (s, 1H), 7.76 (d, J=8.3 Hz, 1H), 7.53 (t, J=7.2 Hz, 1H), 7.44 (d, J=6.9 Hz, 1H), 5.26 (d, J=16.7 Hz, 1H), 5.14 (d, J=16.8 Hz, 1H), 4.77 (t, J=7.0 Hz, 1H), 4.09 (s, 3H), 3.72-3.70 (m, 1H), 3.56-3.47 (m, 2H), 3.40-3.28 (m, 3H), 3.23-3.21 (m, 1H), 2.22-2.19 (m, 1H), 2.00-1.84 (m, 3H); MS (ESI+) m/z 297 (M+H); HPLC 98.3% (AUC), tR 13.35 min.

Sources & evidence

ORD record: ord-c0ae744e4d4e450ca405d51aa48eeda8
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710047B2

Reaction notes

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