Water → HCID 56928637, compound

HRID 510076Notes

Reaction equation

HRID 510076 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:14])OCCCl)=[C:6]([NH2:15])[N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1.O.[O:34]1CC[CH2:36][CH2:35]1>>[NH2:1][C:2]1[N:3]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:5]=[C:6]2[C:7]=1[N:8]([CH2:36][CH2:35][OH:34])[C:9](=[O:14])[NH:15]2

Participants

4

Reactant 3

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 66634903HCID 66634903, compound

Product 1

HCID 56928637HCID 56928637, compound

Conditions

Temperature
0 °C

Procedure

350 mg (0.833 mmol) of the compound obtained in example 6A were initially charged in 12 ml of tetrahydrofuran at 0° C. Then 1.665 ml of a 1M solution of bis(trimethylsilyl)sodium amide in tetrahydrofuran were added dropwise and the mixture was stirred at 0° C. for a further 10 min. The mixture was then stirred at RT overnight. Subsequently, 2 ml of water were added to the mixture, which was concentrated to dryness. The residue was purified by means of preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient). 188 mg of the title compound were obtained (53% of theory).

Workup

  1. stirringThe mixture was then stirred at RT overnight
  2. concentrationwas concentrated to dryness
  3. customThe residue was purified by means of preparative HPLC (acetonitrile/water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-c88f44bb18e5480a9dcfb147703a1d20
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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