1,1,1,3,3,3-Hexafluoro-2-propanol → HCID 57611875, compound

HRID 1919883Notes

Reaction equation

HRID 1919883 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.C(O)(C(F)(F)F)C(F)(F)F.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[C:22]([O:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)=[CH:32][C:31]=1[NH:41][C:42]([C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1)=[O:43])=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[C:22]([O:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)=[CH:32][C:31]=1[NH:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([CH:3]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:2]([OH:6])=[O:5])=[CH:46][CH:45]=1)=[O:43])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 31268PyrrolidineHCID 15620607Glyoxylic acid, monohydrateHCID 57611852HCID 57611852, compound

Product 1

HCID 57611875HCID 57611875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glyoxilic acid monohydrate (0.042 g, 0.456 mmol) was suspended in DCM (2.1 mL)/HFIP (0.2 mL) and pyrrolidine (0.038 mL, 0.456 mmol) and [4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]boronic acid (0.2 g, 0.456 mmol) were added. The reaction was stirred at room temperature overnight. The mixture was transferred to a microwave vial and heated to 120° C. for 30 minutes in the microwave. The solvent was removed in vacuo and the residue triturated in methanol to give the desired product as a pale yellow powder. 1H NMR (DMSO-d6, 600 MHz) δ 9.95 (s, 1H), 8.74 (br s, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.79 (d, J=1.8 Hz, 1H), 7.60 (d, J=8.4 Hz, 2H), 7.49 (m, 2H), 7.43 (d, J=2.4 HZ, 1H), 7.11 (dd, J=5.4 and 3.6 Hz, 1H), 4.33 (s, 1H), 3.06 (m, 2H), 2.79 (m, 2H), 1.84 (m, 4H), 1.43 (s, 9H). MS: cal'd 522 (MH+), exp 522 (MH+).

Workup

  1. additionwere added
  2. temperatureheated to 120° C. for 30 minutes in the microwave
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated in methanol

Sources & evidence

ORD record
ord-532b62bb4efa49a7b9528e1810a7fd60
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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