4-Methylmorpholine → HCID 70651980, compound

HRID 2361396Notes

Reaction equation

HRID 2361396 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][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:36](O)=[O:37])=[N:20][C:19]=2[CH3:39])[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+].F[P-](F)(F)(F)(F)F.[N:50]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.CN1CCOCC1>CN(C=O)C.O>[C:36]([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)=[C:19]([CH3:39])[N:20]=1)=[CH:28][CH:27]=[C:26]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=3)(=[O:37])[NH2:50]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86681527HCID 86681527, compound

Product 1

HCID 70651980HCID 70651980, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-3-methyl-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.5025 g, 0.931 mmol), ammonium chloride (0.199 g, 3.73 mmol), BOP (0.535 g, 1.211 mmol), DIPEA (0.781 ml, 4.47 mmol) and N-methylmorpholine (0.399 ml, 3.63 mmol) in DMF (Volume: 4.66 ml) was stirred under nitrogen for 2.5 h. Water (50 mL) was added, and the solution was stirred for 1 h. The precipitate was filtered, rinsed with water and dried over Drierite to give benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.4856 g, 0.902 mmol, 97% yield) as a tan solid, LC/MS (M+H)=539.24.

Workup

  1. filtrationThe precipitate was filtered
  2. washrinsed with water
  3. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-dd1d8f03989d43db976c80558264947e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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