Water → HCID 57593635, compound

HRID 1785317Notes

Reaction equation

HRID 1785317 reaction equation
CC(C)(O[N:5]([C@H:9]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH2:29][C:30]#[CH:31])[C:25]([Br:32])=[CH:24][N:23]=2)[CH:14]=1)=[O:11])C(=O)[O-])C.S(=O)(=O)(O)O.O>O1CCOCC1>[NH2:5][C@H:9]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH2:29][C:30]#[CH:31])[C:25]([Br:32])=[CH:24][N:23]=2)[CH:14]=1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 86594343HCID 86594343, compound

Product 1

HCID 57593635HCID 57593635, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethoxy[(1R)-2-[[3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-(hydroxymethyl)phenyl]amino]-2-oxo-1-(phenylmethyl)ethyl]carbamate (22 mg) and sulfuric acid (0.3 ml; 2 n) were stirred in dioxane (3 ml) at 100° C. for 2.5 h. After cooling and dilution with water saturated NaHCO3-solution was added and the resulting preticipate collected by filtration yielding the title compound (10 mg).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting preticipate collected by filtration

Sources & evidence

ORD record
ord-f4bdb9387c724a968584a1275d955be4
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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