{3,5-Dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-carbamic acid tert-butyl ester → [2-(4-Amino-2,6-dichlorophenyl)thiazolo[5,4-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine

HRID 2366248Notes

Reaction equation

HRID 2366248 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([C:15]2[S:16][C:17]3[C:18]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=4)=[N:19][CH:20]=[CH:21][C:22]=3[N:23]=2)=[C:10]([Cl:32])[CH:9]=1)(C)(C)C>Cl.O1CCOCC1>[NH2:7][C:8]1[CH:9]=[C:10]([Cl:32])[C:11]([C:15]2[S:16][C:17]3[C:18]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=4)=[N:19][CH:20]=[CH:21][C:22]=3[N:23]=2)=[C:12]([Cl:14])[CH:13]=1

Participants

4

Reactant 1

HCID 68155873{3,5-Dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 66801306[2-(4-Amino-2,6-dichlorophenyl)thiazolo[5,4-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amineYield 75.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of {3,5-dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-carbamic acid tert-butyl ester (235 mg, 0.467 mmol) in 4N HCl in dioxane (10 mL) was heated at 50° C. for 3 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered and the precipitate collected. The solid thus obtained was purified by column chromatography on silica gel eluting with 0-5% 2N NH3/MeOH in EtOAc to afford the title compound as a pale yellow solid (142 mg, 75% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.54 (s, 1H), 8.62 (d, J=1.2 Hz, 1H), 8.41 (d, J=5.6 Hz, 1H), 7.77 (d, J=5.6 Hz, 1H), 7.63 (s, 1H), 6.77 (s, 2H), 6.22 (s, 2H), 2.39 (s, 3H). LCMS (Method C): RT=2.97 min, m/z: 403 [M+H+].

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe precipitate collected
  3. customThe solid thus obtained
  4. customwas purified by column chromatography on silica gel eluting with 0-5% 2N NH3/MeOH in EtOAc

Sources & evidence

ORD record
ord-db57630bb52f4e5eb7dbb9119689434c
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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