Diisopropylethylamine → 2-[(Isoquinoline-3-carbonyl)-amino]-benzooxazole-7-carboxylic acid methyl ester

HRID 1845097Notes

Reaction equation

HRID 1845097 reaction equation
O.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[N:3]=1.[CH3:15][O:16][C:17]([C:19]1[C:27]2[O:26][C:25]([NH2:28])=[N:24][C:23]=2[CH:22]=[CH:21][CH:20]=1)=[O:18].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][O:16][C:17]([C:19]1[C:27]2[O:26][C:25]([NH:28][C:12]([C:4]3[N:3]=[CH:2][C:11]4[C:6]([CH:5]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[O:14])=[N:24][C:23]=2[CH:22]=[CH:21][CH:20]=1)=[O:18]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27367043-Isoquinolinecarboxylic acid hydrateHCID 66940222Methyl 2-amino-1,3-benzoxazole-7-carboxylate

Product 1

HCID 669403112-[(Isoquinoline-3-carbonyl)-amino]-benzooxazole-7-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(Isoquinoline-3-carbonyl)-amino]-benzooxazole-7-carboxylic acid methyl ester was prepared according to general procedure A using 1.052 g (5.5 mmol) of isoquinoline 3-carboxylic acid hydrate, 797 mg (4.15 mmol) of 2-amino-benzooxazole-7-carboxylic acid methyl ester, 2.09 g (5.5 mmol) of HBTU, 1.58 mL (9 mmol) of DIEA and 14 mL of DMF stirring at 90° C. for 3 h. 684 mg (1.97 mmol, 48%) of the product was obtained. LCMS: 348 (M+1)+.

Sources & evidence

ORD record
ord-078b007044514412847db0cc0a70713b
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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