Lithium Hydroxide → HCID 58551222, compound

HRID 1908192Notes

Reaction equation

HRID 1908192 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:33]3[C:34]([C:37]#[N:38])=[CH:35][CH:36]=[C:32]3[C:12]3([CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH:28]([CH3:30])[CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)[O:11][C:10]=2[CH:39]=1)(=O)C.[Li+].[OH-].C1COCC1>CO>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:33]3[C:34]([C:37]#[N:38])=[CH:35][CH:36]=[C:32]3[C:12]3([CH2:17][CH2:16][N:15]([C:18](=[O:31])[C:19]4[CH:20]=[CH:21][C:22]([S:25]([CH:28]([CH3:29])[CH3:30])(=[O:27])=[O:26])=[CH:23][CH:24]=4)[CH2:14][CH2:13]3)[O:11][C:10]=2[CH:39]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58550927HCID 58550927, compound

Product 1

HCID 58551222HCID 58551222, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1-Cyano-1′-(4-(isopropylsulfonyl)benzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-yl)methyl acetate (16.2 mg, 0.0297 mmol) was treated with 1M LiOH (1 mL), THF (5 mL) and MeOH (1 mL). The mixture was stirred at room temperature over night. The volatiles were removed and the residue was neutralized with 1N HCl. The mixture was extracted with CH2Cl2 (2×). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to give 7′-(hydroxymethyl)-1-(4-isopropylsulfonylbenzoyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbonitrile (11.3 mg, 75%). ESI-MS m/z calc. 505.58. found 506.5 (M+1)+; Retention time 1.49 minutes (3 min run). NMR (400 MHz, DMSO) δ 7.93 (dd, J=8.2, 6.5 Hz, 3H), 7.73 (d, J=8.3 Hz, 2H), 7.32 (d, J=4.0 Hz, 1H), 7.25 (s, 1H), 7.15 (d, J=8.4 Hz, 1H), 6.45 (d, J=4.1 Hz, 1H), 5.39-5.30 (m, 1H), 4.51 (s, 2H), 3.81-3.64 (m, 1H), 3.54-3.42 (m, 2H), 3.41-3.37 (m, 1H), 2.20-2.12 (m, 1H), 2.13-2.03 (m, 1H), 2.01 (t, J=5.9 Hz, 1H), 1.57 (dd, J=12.5, 6.2 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H).

Workup

  1. customThe volatiles were removed
  2. extractionThe mixture was extracted with CH2Cl2 (2×)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4eca7500c7a54ba7a9912b9fe2968041
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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