Hydrochloric Acid → HCID 57397897, compound

HRID 1177661Notes

Reaction equation

HRID 1177661 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH2:28])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.O.[C:30]([OH:34])(=[O:33])[CH:31]=O.Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH:28][CH2:31][C:30]([OH:34])=[O:33])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15620607Glyoxylic acid, monohydrateHCID 57397896HCID 57397896, compound

Product 1

HCID 57397897HCID 57397897, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-ethanamine (83 mg, 0.213 mmol) was added glyoxylic acid monohydrate (39 mg, 0.426 mmol) and DCM (1 mL) before it was stirred for 5 h at ambient temperature. The reaction mixture was concentrated before adding concentrated hydrochloric acid (2.13 mL, 4.26 mmol) and heating to reflux for 16 h. The reaction mixture was diluted with 75 mL of DCM, added to a separatory funnel, partitioned with water, washed 1 time with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after preparatory LC. MS (ESI) m/z: Calculated: 447.1; Observed: 448.1 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. temperatureheating
  3. temperatureto reflux for 16 h
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed 1 time with 50 mL of water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-f71e499ee2474ff4b450298188f0709d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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