4-Methylmorpholine → HCID 67994827, compound

HRID 2361314Notes

Reaction equation

HRID 2361314 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:47])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([N:31]5[CH2:35][CH2:34][CH:33]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:32]5)=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:44](O)=[O:45])=[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:57]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>[Si:37]([O:36][CH:33]1[CH2:34][CH2:35][N:31]([C:26]2[CH:25]=[C:24]3[C:29]([C:30]4[C:18]([C:14]5[C:13]([CH3:47])=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]6[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=6)[CH:17]=[CH:16][CH:15]=5)=[CH:19][N:20]=[C:21]([C:44](=[O:45])[NH2:57])[C:22]=4[NH:23]3)=[CH:28][CH:27]=2)[CH2:32]1)([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:39])[CH3:38]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67994707HCID 67994707, compound

Product 1

HCID 67994827HCID 67994827, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A burgundy, homogeneous solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.1323 g, 0.203 mmol), ammonium chloride (0.043 g, 0.813 mmol), BOP (0.117 g, 0.264 mmol), DIPEA (0.170 mL, 0.976 mmol) and N-methylmorpholine (0.087 mL, 0.793 mmol) in DMF (1.694 mL) was stirred for 1 h. Water (20 mL) was added, and the precipitate was filtered and dried over Drierite to give benzyl the desired product (0.1164 g, 0.179 mmol, 88% yield) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-8f5baac4cc994dcf9b97bec230be15b2
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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