Hydrochloric Acid → HCID 178497693, compound

HRID 2369896Notes

Reaction equation

HRID 2369896 reaction equation
CC1C=C(C([O-])=O)C2C(CCN[C@H]3C4CCN(CC4)C3)=NNC=2C=1.[Li+].[CH3:26][C:27]1[CH:28]=[C:29]([C:47]([O:49][CH3:50])=[O:48])[C:30]2[C:31]([CH2:36][CH2:37][NH:38][C@H:39]3[CH:44]4[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]4)[CH2:40]3)=[N:32][NH:33][C:34]=2[CH:35]=1.[ClH:51]>>[ClH:51].[CH3:26][C:27]1[CH:28]=[C:29]([C:47]([O:49][CH3:50])=[O:48])[C:30]2[C:31]([CH2:36][CH2:37][NH:38][C@H:39]3[CH:44]4[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]4)[CH2:40]3)=[N:32][NH:33][C:34]=2[CH:35]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 178427216HCID 178427216, compoundHCID 178497692HCID 178497692, compound

Product 1

HCID 178497693HCID 178497693, compound

Procedure

The procedure described in Step F of Example 8 was used to convert lithium (S)-6-methyl-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate from Step D above to (S)-methyl 6-methyl-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate (43 mg, 17%) as an off-white solid, which was treated immediately with hydrochloric acid following the procedure described in Step G of Example 8 to afford (S)-methyl 6-methyl-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate hydrochloride as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.06 (s, 1H), 8.04 (s, 1H), 7.82 (s, 1H), 4.73-4.65 (m, 1H), 4.14-3.99 (m, 2H), 3.83-3.71 (m, 2H), 3.45-3.41 (m, 3H), 2.54 (d, J=2.5 Hz, 1H), 2.51 (s, 3H), 2.28 (br s 1H), 2.17-2.10 (m, 2H), 2.10-1.99 (m, 1H); MS (ESI) m/z 311 (M+H).

Sources & evidence

ORD record
ord-d8908d8ecc0a45888309086ec7142f87
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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