Hydrochloric Acid → 2-Amino-2-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)propane-1,3-diol hydrochloride

HRID 1177505Notes

Reaction equation

HRID 1177505 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][C:28]([NH:33]C(=O)C)([CH2:31][OH:32])[CH2:29][OH:30])[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.[ClH:37]>>[ClH:37].[NH2:33][C:28]([CH2:27][CH2:26][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:19][CH2:18]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1)([CH2:31][OH:32])[CH2:29][OH:30]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67111774N-(4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-1-hydroxy-2-(hydroxymethyl)butan-2-yl)acetamide

Product 1

HCID 671121642-Amino-2-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)propane-1,3-diol hydrochloride

Procedure

A slurry of N-(4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-1-hydroxy-2-(hydroxymethyl)butan-2-yl)acetamide (0.205 g, 0.405 mmol) in 6 mL 5N aq. HCl was heated to 120° C. in a sealed tube. A clear yellow solution resulted, with a white precipitate forming after 1 h. The mixture was heated overnight to give a gray mixture, which was cooled and filtered through a glass frit, rinsing with water and EtOH, and the solid was dried in vacuo to give 2-amino-2-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethyl)propane-1,3-diol hydrochloride as an off-white solid. MS (ESI) m/z: calculated: 463.2; Observed: 464.1 (M++1).

Workup

  1. customA clear yellow solution resulted, with a white precipitate
  2. customforming after 1 h
  3. temperatureThe mixture was heated overnight
  4. customto give a gray mixture, which
  5. temperaturewas cooled
  6. filtrationfiltered through a glass frit
  7. washrinsing with water and EtOH
  8. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-c0ef99caa9fe4162b8d5d7712b697e8c
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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