Dichloromethane → HCID 58464730, compound

HRID 1185413Notes

Reaction equation

HRID 1185413 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[N:29]=[C:30]([C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH:47]=[CH2:48])[C:42]=3[F:49])[S:31][C:32]=2[NH:33]C(=O)OC(C)(C)C)=[O:27])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1.[H][H].B(Br)(Br)Br.C(Cl)Cl>CO>[NH2:33][C:32]1[S:31][C:30]([C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][CH3:48])[C:42]=2[F:49])=[N:29][C:28]=1[C:26]([NH:25][C:20]1[CH:21]=[N:22][N:23]([CH3:24])[C:19]=1[N:15]1[CH2:16][CH2:17][CH2:18][C@@H:12]([NH2:11])[CH2:13][CH2:14]1)=[O:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 58464904HCID 58464904, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58464730HCID 58464730, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl N-[4-[[5-[(4R)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-(2-fluoro-3-vinyl-phenyl)thiazol-5-yl]carbamate (51 mg, 0.086 mmol) was dissolved in methanol (50 mL) and hydrogenated on H-Cube at 60° C. and 50 bar hydrogen pressure to reduce the double bond. The solution was concentrated and the residue was dissolved in DCM (5 mL). 1.0M solution of boron tribromide in methylene chloride (0.35 ml, 0.35 mmol) was added and the mixture was stirred for 2 h. The solvent was distilled off and the residue was purified via reverse phase HPLC to afford 383. MS (ESI) m/z: 458.3 [M+H+].

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in DCM (5 mL)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-79b431090fe04f32bae5abade728ea55
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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