HCID 67111738, compound → HCID 59174829, compound

HRID 1177617Notes

Reaction equation

HRID 1177617 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][C:27]([NH:32]C(=O)C)([CH2:30][OH:31])[CH2:28][OH:29])[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>Cl>[NH2:32][C: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)([CH2:30][OH:31])[CH2:28][OH:29]

Participants

3

Reactant 1

HCID 67111738HCID 67111738, compound

Product 1

HCID 59174829HCID 59174829, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a sealable tube a slurry of N-(3-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenyl)-1-hydroxy-2-(hydroxymethyl)propan-2-yl)acetamide (0.14 g, 0.28 mmol) in hydrochloric acid, 5 N (5.00 mL, 165 mmol) was heated to 120° C. The heterogeneous reaction mixture turned light green after 2 h of heating. The reaction mixture was cooled, filtered through a glass frit, and the solid was rinsed with water, EtOH, and CHCl3. The EtOH and CHCl3 filtrate was combined and concentrated, and this was combined with the isolated solid, and the material was purified by SFC (Sepapak 2 (250×21 mm, 5 micron) column using 50% methanol with 0.2% DEA as additive in supercritical CO2 with a flow rate of 60 mL/min) to give 2-amino-2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)propane-1,3-diol. MS (ESI) m/z: calculated: 449.2; Observed: 450.0 (M++1).

Workup

  1. temperatureof heating
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through a glass frit
  4. washthe solid was rinsed with water, EtOH, and CHCl3
  5. concentrationconcentrated
  6. customthe material was purified by SFC (Sepapak 2 (250×21 mm, 5 micron) column

Sources & evidence

ORD record
ord-8c5ca07c6cde44e59ff928905dfb80e8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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