Hydrochloric Acid → HCID 70896187, compound

HRID 2369894Notes

Reaction equation

COC1C=C(C([O-])=O)C2C(CCN[C@H]3C4CCN(CC4)C3)=NNC=2C=1.[Li+].[CH3:27][O:28][C:29]1[C:40]2[C:41]3[N:33]([NH:34][CH2:35][C:36]=3[C@H:37]([CH:43]3[CH:48]4[CH2:49][CH2:50][N:45]([CH2:46][CH2:47]4)[CH2:44]3)[C:38](=[O:42])[CH:39]=2)[CH:32]=[CH:31][N:30]=1.[ClH:51]>>[ClH:51].[CH3:27][O:28][C:29]1[C:40]2[C:41]3[N:33]([NH:34][CH2:35][C:36]=3[C@H:37]([CH:43]3[CH:48]4[CH2:47][CH2:46][N:45]([CH2:50][CH2:49]4)[CH2:44]3)[C:38](=[O:42])[CH:39]=2)[CH:32]=[CH:31][N:30]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 66898173HCID 66898173, compound

HCID 178492731HCID 178492731, compound

Product 1

HCID 70896187HCID 70896187, compoundYield 39%

Procedure

The procedure described in Step F of Example 8 was used to convert lithium (S)-6-methoxy-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate from Step J above to (S)-4-methoxy-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-methoxy-7-(quinuclidin-3-yl)-8,9-dihydro-[1,4]diazepino[6,7,1-hi]indazol-6(7H)-one hydrochloride (60 mg, 39%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 8.05 (s, 1H), 7.83 (dd, J=2.5 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 4.72-4.65 (m, 3H), 4.14-4.00 (m, 2H), 3.89 (s, 3H), 3.86-3.71 (m, 2H), 3.45-3.35 (m, 4H), 2.54 (d, J=2.5 Hz, 1H), 2.28 (brs 1H), 2.15-2.11 (m, 2H), 2.20-1.99 (m, 1H); MS (ESI+) m/z 327 (M+H).

Sources & evidence

ORD record: ord-5fe12e1f3fc047c987eaf281aad2080f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710046B2

Reaction notes

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