1-Hydroxybenzotriazole → HCID 90221098, compound

HRID 1481906Notes

Reaction equation

HRID 1481906 reaction equation
Cl.[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[CH3:22])[C:7]2[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:6]=2[NH:5][CH2:4]1.[N:29]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([CH3:35])[C@H:30]([C:32](O)=[O:33])[CH3:31].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:39]([O:38][C:36](=[O:37])[N:29]([C@H:30]([C:32](=[O:33])[NH:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:13]=2[CH3:22])[C:7]2[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:6]=2[NH:5][CH2:4]1)[CH3:31])[CH3:35])([CH3:40])([CH3:41])[CH3:42]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 90220939HCID 90220939, compound

Product 1

HCID 90221098HCID 90221098, compoundYield 92.54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (S)-3-amino-1-(2-methyl-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5 tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (305 mg, 0.778 mmol) in DMF (10 mL) was added Boc-N-Me-Ala-OH (173.912 mg, 0.856 mmol), HOBT (115.645 mg, 0.856 mmol) and DIPEA (0.67 mL, 3.89 mmol). After 10 min, the mixture was cooled to 0° C. and HBTU (324.63 mg, 0.856 mmol) was added. After 2 h, the mixture was diluted with ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound (390 mg, 92.54%) as an off white solid. LC-MS: 542.0 (M+H).

Workup

  1. waitAfter 2 h
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-76bbca6ba9b940ee83500e5ea5ca0c73
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

Loading…