4-Methylmorpholine → HCID 86681521, compound

HRID 2361321Notes

Reaction equation

HRID 2361321 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:44])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([NH:31][C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:41]([OH:43])=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:54]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>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([CH3:44])=[C:14]([C:18]2[C:30]3[C:29]4[C:24](=[CH:25][C:26]([NH:31][C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:39])([CH3:38])[CH3:40])=[O:33])=[CH:27][CH:28]=4)[NH:23][C:22]=3[C:21]([C:41]([NH2:54])=[O:43])=[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

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67994548HCID 67994548, compound

Product 1

HCID 86681521HCID 86681521, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a dark, homogeneous solution of 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-((2-(trimethylsilyl)ethoxy)carbonylamino)-9H-pyrido[3,4-b]indole-1-carboxylic acid (0.4181 g, 0.685 mmol) in DMF (2.74 mL) were added ammonium chloride (0.146 g, 2.74 mmol), BOP (0.394 g, 0.890 mmol), DIPEA (0.574 mL, 3.29 mmol) and N-methylmorpholine (0.294 mL, 2.67 mmol). After 2.5 hr, water was added, and the precipitate was collected and dried over Drierite to give the desired product (0.365 g, 0.599 mmol, 87% yield) as a light brown solid.

Workup

  1. customthe precipitate was collected
  2. dry with materialdried over Drierite

Sources & evidence

ORD record
ord-ba13951a53784887a84ab1ac55f52fe5
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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