4-Methylmorpholine → Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

HRID 2361347Notes

Reaction equation

HRID 2361347 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][CH:26]=[C:27]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[CH:28]=4)[NH:23][C:22]=3[C:21]([C:37]([OH:39])=O)=[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+].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: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][C:27]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[CH:26][CH:25]=3)(=[O:39])[NH2:50]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 679949964-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid

Product 1

HCID 67994849Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamateYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.1408 g, 0.262 mmol), ammonium chloride (0.056 g, 1.050 mmol), BOP (0.151 g, 0.341 mmol), DIPEA (0.220 mL, 1.260 mmol) and N-methylmorpholine (0.113 mL, 1.023 mmol) in DMF (2.187 mL) was stirred for 1 hr. Water (22 mL) was added, and the precipitate was filtered, washed with water, dried over Drierite to give the desired product (0.1277 g, 0.231 mmol, 88% yield) as a light tan solid.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-4514f36ef0f44d24a98845d2cce12acf
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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