2-Amino-2-methyl-1-propanol → HCID 178454594, compound

HRID 518729Notes

Reaction equation

HRID 518729 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20](Cl)=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[NH2:36][C:37]([CH3:41])([CH3:40])[CH2:38][OH:39]>C1COCC1>[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@H:14]2[CH2:19][CH2:18][C@@H:17]([C:20](=[O:21])[NH:36][C:37]([CH3:41])([CH3:40])[CH2:38][OH:39])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 178522615HCID 178522615, compound

Product 1

HCID 178454594HCID 178454594, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. suspension of cis-4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarbonyl chloride (50 mg, 0.100 mmol) in THF (1 mL) was added 2-amino-2-methylpropan-1-ol (17.8 mg, 0.401 mmol). The mixture was stirred for 1 hour at RT. The solvent was removed, and the residue was purified by reverse-phase preparative HPLC, using 0.1% NH4OH in ACN/water. The product fractions were combined and concentrated to provide (E)-4-fluoro-N-(1-(cis-4-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)cyclohexyl)-6-(morpholinomethyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide as a white powder (8.5 mg, 15.4% yield). MS, m/z (C30H38FN5O4): calcd, 551.3. found, 552.4 [M+H].

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by reverse-phase preparative HPLC
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e00adfe9597340a685b7959606f38c1a
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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