Ammonia → HCID 86667312, compound

HRID 1040920Notes

Reaction equation

HRID 1040920 reaction equation
[Cl:1][C:2]1[C:3]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=N[C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:19][CH2:20]OC(=O)C)[CH2:16][CH2:15][N:14]([CH3:25])[C:13]=3[CH:26]=2)=[N:6][CH:7]=1.O1[CH2:44][CH2:43]OCC1.[Li+].[OH-:46].[NH3:47]>CO.ClCCl>[Cl:1][C:2]1[C:3]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[N:47][C:5]([N:8]([C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:19][CH2:20][OH:46])[CH2:16][CH2:15][N:14]([CH3:25])[C:13]=3[CH:26]=2)[C:44]2[CH:43]=[CH:13][CH:26]=[CH:9][CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67263814HCID 67263814, compound

Product 1

HCID 86667312HCID 86667312, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 25 ml round bottom flask, acetic acid 2-{8-[5-chloro-4-((1R,2R)-2-methanesulfonylamino-cyclohexylamino)-pyrimidin-2-ylamino]-1-methyl-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl}-ethyl ester (50 mg, 0.09 mmole), dioxane (5 ml), and 1M LiOH (1 mL, 1 mmole) were added and stirred at room temperature for 18 hours. The reaction was then acidified to pH 2 with 1NHCl. The solvents were removed under vacuum to give a white solid. The desired product (10 mg, 21% yield) was isolated via column chromatography with dichloromethane and ammonia in methanol as eluant. NMR 1H-(CDCl3)-δ-7.93 (s, 1H), 7.15 (d, 1H, J=7.83 Hz), 7.04 (d, 1H, J=7.83 Hz), 6.93 (s, 1H), 6.89 (s, 1H), 5.38 (d, 1H, J=5.73 Hz), 5.29 (s, 1H), 3.82-3.95 (m, 1H), 3.80 (s, 2H), 3.61 (t, 2H, J=5.31 Hz), 3.15-3.30 (m, 1H), 2.99 (bs, 4H), 2.91 (s, 3H), 2.78 (s, 3H), 2.61 (t, 2H, J=5.30 Hz), 2.10-2.30 (m, 2H), 1.75-1.90 (m, 2H), 1.30-1.50 (m, 4H) LCMS (ESI+) 524.38 (M+H); MP=181-190° C.

Workup

  1. customThe solvents were removed under vacuum
  2. customto give a white solid

Sources & evidence

ORD record
ord-af6f4d14df0d4a368368b348ee228a62
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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