Methyl Isocyanate → HCID 67473768, compound

HRID 1516337Notes

Reaction equation

HRID 1516337 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][C@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:18]4[CH2:23][CH2:22][N:21]([CH:24]5[CH2:27][O:26][CH2:25]5)[CH2:20][CH2:19]4)[CH:16]=3)[CH2:11][C@@H:10]2[OH:28])=[O:7])=[CH:4][CH:3]=1.N1(C2C=CN=CC=2)CCCC1.[CH3:42][N:43]=[C:44]=[O:45]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:18]4[CH2:19][CH2:20][N:21]([CH:24]5[CH2:27][O:26][CH2:25]5)[CH2:22][CH2:23]4)[CH:16]=3)[CH2:11][C@@H:10]2[O:28][C:44](=[O:45])[NH:43][CH3:42])=[O:7])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 755674-PyrrolidinopyridineHCID 67280601HCID 67280601, compound

Product 1

HCID 67473768HCID 67473768, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoro-N-[(1S,2S)-2-hydroxy-6-[4-(oxetan-3-yl)piperazin-1-yl]indan-1-yl]benzamide (220 mg, 0.535 mmol) in tetrahydrofuran (3.0 mL) add 4-pyrrolidinopyridine (16 mg, 0.107 mmol) and seal in a pressure vial. Add methyl isocyanate (97 μL, 1.60 mmol) by syringe to the mixture and stir at 60° C. overnight. Cool the resulting suspension in an ice bath, collect the white solid by filtration, and dry in a vacuum oven at 40° C. for 3 hr. to obtain the title compound (200 mg, 80%). LC-ES/MS m/z 469 [M+H]+.

Workup

  1. customseal in a pressure vial
  2. temperatureCool the resulting suspension in an ice bath
  3. customcollect the white solid
  4. filtrationby filtration
  5. customdry in a vacuum oven at 40° C. for 3 hr

Sources & evidence

ORD record
ord-313881026ae0463fa51d40fcee1178b6
Source dataset
uspto-grants-2012_07
Patent number
US08227468B2

Reaction notes

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