Hydrochloric Acid → HCID 57463078, compound

HRID 1783839Notes

Reaction equation

HRID 1783839 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:28]4[C:24]([S:25][CH:26]=[CH:27]4)=[N:23][C:22]=3[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35](=[O:37])[NH2:36])[CH:30]=3)[CH:18]=[CH:17][N:16]=2)[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:28]4[C:24]([S:25][CH:26]=[CH:27]4)=[N:23][C:22]=3[C:29]3[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=3)[C:35]([NH2:36])=[O:37])[CH:18]=[CH:17][N:16]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57590768HCID 57590768, compound

Product 1

HCID 57463078HCID 57463078, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-3-{4-[6-(3-carbamoyl-phenyl)-imidazo[2,1-b]thiazol-5-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.289 mmol) was dissolved in 3 mL of ethyl acetate and treated with 3 ml of 3.0 M HCl in ethyl acetate at room temperature (RT) overnight. Solid product was filtered, washed ethyl acetate and dried under vacuum overnight to provide 0.130 g (97%) of the title compound as a yellow solid. M.p.=202-205° C. 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 9.35 (br. s, 1H), 9.20-8.25 (bs, 3H), 8.12-8.09 (m, 2H), 7.98-7.968.0 (m, 1H), 7.74-7.72 (m, 1H), 7.57-7.52 (m, 2H), 7.25 (bs, 1H), 6.40 (d, J=6.0 Hz, 1H), 4.31 (br. s, 1H), 3.40 (d, J=9.2 Hz, 1H), 3.16-3.13 (m, 1H), 2.94-2.90 (m, 2H), 2.03-1.97 (m, 1H), 1.96-1.89 (m, 1H), 1.89-1.80 (bs, 1 H), 1.66-1.60 (m, 1H); LCMS: 459 [M+H]. calc. for C21H21N7OS.3.14(HCl).0.25(EtOAc) C, 47.52; H, 4.74; N, 17.63. Found C, 47.57; H, 4.44; N, 17.52; LCMS: 420 [M+H].

Workup

  1. filtrationSolid product was filtered
  2. washwashed ethyl acetate
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-d1761b5fdfe44dc7a2349407925282f7
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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