Hydrochloric Acid → N-((S)-2-amino-3-(3-chlorophenyl)propyl)-4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-amine

HRID 2109703Notes

Reaction equation

HRID 2109703 reaction equation
[NH2:1][C@@H:2]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[CH2:3][N:4]([C:8]1[S:9][C:10]([C:16]2[S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[N:24]=2)=[C:11]([CH2:13][O:14][CH3:15])[N:12]=1)C(=O)C.C1COCC1.Cl.[OH-].[Na+]>>[NH2:1][C@@H:2]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[CH2:3][NH:4][C:8]1[S:9][C:10]([C:16]2[S:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[N:24]=2)=[C:11]([CH2:13][O:14][CH3:15])[N:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23653700N-((S)-2-amino-3-(3-chlorophenyl)propyl)-N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamide

Product 1

HCID 23653778N-((S)-2-amino-3-(3-chlorophenyl)propyl)-4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-amineYield 38%

Conditions

Temperature
150 °C

Procedure

A glass microwave reaction vessel was charged with N-((S)-2-amino-3-(3-chlorophenyl)propyl)-N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamide (0.090 g, 0.1 8 mmol), THF (2.0 mL, 24 mmol), and 5 N HCl (2.0 mL, 10.0 mmol). The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 150° C. for 11 minutes. The solution was then made basic with 10 N NaOH and extracted with EtOAc. The solvent was removed, and the compound was purified by reverse phase HPLC to give the title compound (31 mg, 38%). LCMS (M+H) 445.7 calc. for C20H21ClN5OS2 446.09. 1H NMR (400 MHz, CD3OD): δ ppm 9.12 (s, 1H), 8.50 (d, J=5.7 Hz, 1H), 7.83 (d, J=5.7 Hz, 1H), 7.34 (s, 1H), 7.23 (m, 3H), 4.70 (dd, J=12.4, 17.4 Hz, 2H), 4.46 (m, 1H), 3.47 (s, 3H), 3.25 (dd, J=3.7, 13.2 Hz, 1H), 3.15 (dd, J=9.9, 13.2 Hz, 1H), 2.98 (m, 2H).

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with EtOAc
  3. customThe solvent was removed
  4. customthe compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-96e6bdea88f84f09b5f199b920b3bee7
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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