Hydrochloric Acid → N-{3-[2-(1-aminocyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-cyclopropylpyrimidin-2-amine hydrochloride

HRID 1040071Notes

Reaction equation

HRID 1040071 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]3[CH:12]=[C:13]([C:18]4[S:22][C:21]([C:23]5([NH:27]S(C(C)(C)C)=O)[CH2:26][CH2:25][CH2:24]5)=[N:20][CH:19]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)[N:5]=2)[CH2:3][CH2:2]1.[ClH:34]>O1CCOCC1>[ClH:34].[NH2:27][C:23]1([C:21]2[S:22][C:18]([C:13]3[CH:12]=[C:11]([NH:10][C:6]4[N:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[CH:9]=[CH:8][N:7]=4)[CH:16]=[C:15]([CH3:17])[CH:14]=3)=[CH:19][N:20]=2)[CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67247850N-[1-(5-{3-[(4-cyclopropylpyrimidin-2-yl)amino]-5-methylphenyl}-1,3-thiazol-2-yl)cyclobutyl]-2-methylpropane-2-sulfinamide

Product 1

HCID 67256485N-{3-[2-(1-aminocyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-cyclopropylpyrimidin-2-amine hydrochlorideYield 109%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the product of Step 2 (182 mg, 0.38 mmol) in dioxane (3.8 mL) was added hydrochloric acid 4.0 M in dioxane (0.95 mL, 3.78 mmol) and the mixture was stirred for at room temperature for 2 h. The mixture was concentrated under reduced pressure to provide 170 mg (0.41 mmol, 109%) of N-{3-[2-(1-aminocyclobutyl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-cyclopropylpyrimidin-2-amine hydrochloride. MS ESI: [M+H]+ m/z 378.2. 1H NMR (600 MHz, d6-DMSO) δ 9.54 (s, 1H), 8.95 (s, 2H), 8.25 (d, J=4.8, 1H), 8.16 (s, 1H), 8.10 (s, 1H), 7.40 (s, 1H), 7.11 (s, 1H), 6.83 (d, J=4.8, 1H), 2.66 (m, 2H), 2.57 (m, 2H), 2.28 (s, 3H), 2.14 (m, 1H), 2.03 (m, 2H), 1.10-1.04 (m, 4H). rhSYK activity=+++

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81e0c1d3bc684838a6892786e2045b90
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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