Hydrochloric Acid → HCID 131729462, compound

HRID 1887510Notes

Reaction equation

CN1C2C=CC=C(C([O-])=O)C=2C(CN[C@@H]2C3CCN(CC3)C2)=N1.[CH3:24][N:25]1[C:29]2[CH:30]=[N:31][CH:32]=[C:33]3[C:34](=[O:45])[C@H:35]([CH:37]4[CH:42]5[CH2:43][CH2:44][N:39]([CH2:40][CH2:41]5)[CH2:38]4)[CH2:36][C:27]([C:28]=23)=[N:26]1.[ClH:46]>>[ClH:46].[CH3:24][N:25]1[C:29]2[CH:30]=[N:31][CH:32]=[C:33]3[C:34](=[O:45])[C@@H:35]([CH:37]4[CH:42]5[CH2:41][CH2:40][N:39]([CH2:44][CH2:43]5)[CH2:38]4)[CH2:36][C:27]([C:28]=23)=[N:26]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 66772595HCID 66772595, compound

HCID 86636561HCID 86636561, compound

Product 1

HCID 131729462HCID 131729462, compound

Procedure

Following general procedure GP-H, (R)-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 treated with hydrochloric acid following general procedure GP-I to give (R)-2-methyl-7-(quinuclidin-3-yl)-7,8-dihydropyrazolo[3,4,5-de]isoquinolin-6(2H)-one, hydrochloride salt: 1H NMR (500 MHz, DMSO-d6) δ 10.20 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.53 (t, J=7.0 Hz, 1H), 7.40 (d, J=6.5 Hz, 1H), 5.27 (d, J=17.0 Hz, 1H), 5.15 (d, J=16.5 Hz, 1H), 4.77 (t, J=9.0 Hz, 1H), 4.08 (s, 3H), 3.72-3.69 (m, 1H), 3.58-3.48 (m, 2H), 3.40-3.28 (m, 2H), 3.22-3.18 (m, 1H), 2.46-2.42 (m, 1H), 2.28-2.14 (m, 1H), 2.08-1.84 (m, 3H); MS (ESI+) m/z 297 (M+H); HPLC 98.7% (AUC), tR 13.39 min.

Sources & evidence

ORD record: ord-5c7ecef6005549cd9ad3d1dc27af655d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501729B2

Reaction notes

Loading…