4-Methylmorpholine → Benzyl 3-(1-carbamoyl-7-(tetrahydrofuran-3-yloxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

HRID 2361303Notes

Reaction equation

HRID 2361303 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:40])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([O:31][CH:32]5[CH2:36][CH2:35][O:34][CH2:33]5)=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:37](O)=[O:38])=[N:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C([N:46](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.O>[C:37]([C:21]1[C:22]2[NH:23][C:24]3[C:29]([C:30]=2[C:18]([C:14]2[C:13]([CH3:40])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:17]=[CH:16][CH:15]=2)=[CH:19][N:20]=1)=[CH:28][CH:27]=[C:26]([O:31][CH:32]1[CH2:36][CH2:35][O:34][CH2:33]1)[CH:25]=3)(=[O:38])[NH2:46]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 706509694-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-(tetrahydrofuran-3-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid

Product 1

HCID 67994800Benzyl 3-(1-carbamoyl-7-(tetrahydrofuran-3-yloxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamateYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(tetrahydrofuran-3-yloxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.195 g, 0.363 mmol), ammonium chloride (0.078 g, 1.451 mmol), N,N-diisopropylethylamine (0.304 mL, 1.741 mmol), BOP (0.209 g, 0.472 mmol), and N-methylmorpholine (0.156 mL, 1.415 mmol) in N,N-dimethylformamide (3 mL) was stirred at room temperature for 1.5 hr. To the reaction mixture was added water (30 mL), and the resulting mixture was stirred at room temperature for 30 min. The insoluble product (0.189 g, 0.352 mmol, 97% yield) was collected as a beige solid by suction filtration and dried over Drierite under vacuum.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 min

Sources & evidence

ORD record
ord-bb990741295f47de860b38cc181733ad
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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