Hydrochloric Acid → HCID 70896168, compound

HRID 2369888Notes

Reaction equation

N12CCC(CC1)[C@H](NCCC1C3C(C([O-])=O)=CC=CC=3NN=1)C2.[Li+].[F:25][C:26]1[C:37]2[C:38]3[N:30]([NH:31][CH2:32][C:33]=3[C@H:34]([CH:40]3[CH:45]4[CH2:46][CH2:47][N:42]([CH2:43][CH2:44]4)[CH2:41]3)[C:35](=[O:39])[CH:36]=2)[CH:29]=[CH:28][N:27]=1.[ClH:48]>>[ClH:48].[F:25][C:26]1[C:37]2[C:38]3[N:30]([NH:31][CH2:32][C:33]=3[C@H:34]([CH:40]3[CH:45]4[CH2:46][CH2:47][N:42]([CH2:43][CH2:44]4)[CH2:41]3)[C:35](=[O:39])[CH:36]=2)[CH:29]=[CH:28][N:27]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 66898818HCID 66898818, compound

HCID 178524259HCID 178524259, compound

Product 1

HCID 70896168HCID 70896168, compoundYield 71%

Procedure

The procedure described in Step F of Example 8 was used to convert lithium (S)-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate from Step H above to (S)-4-fluoro-7-(quinuclidin-3-yl)-8,9-dihydro-[1,4]diazepino[6,7,1-hi]indazol-6(7H)-one, which was treated immediately with hydrochloric acid following the procedure described in Step G of Example 8 to afford (S)-4-fluoro-7-(quinuclidin-3-yl)-8,9-dihydro-[1,4]diazepino[6,7,1-hi]indazol-6(7H)-one hydrochloride (30 mg, 71%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 8.13 (s, 1H), 7.93 (dd, J=10.0, 3.0, 1H), 7.71 (dd, J=9.0, 3.0 Hz, 1H), 4.74 (t, J=4.0 Hz, 2H), 4.60 (bs, 1H), 4.30 (bs, 1H), 4.03 (bs, 1H), 3.68 (s, 1H), 3.19-3.14 (m, 2H), 2.99-2.91 (m, 3H), 2.16 (dd, J=6.0, 2.0 Hz, 1H), 1.91-1.88 (m, 2H), 1.82-1.80 (m, 1H), 1.68 (s, 1H); MS (ESI+) m/z 315 (M+H).

Sources & evidence

ORD record: ord-7eeb66a08f264b0dad0b4e707321fb4f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710046B2

Reaction notes

Loading…