[4-(3-{6-[(Thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester → HCID 66546523, compound

HRID 1186559Notes

Reaction equation

HRID 1186559 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]3[N:17]([C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][CH2:31][C:32]5[CH:36]=[CH:35][S:34][CH:33]=5)[N:25]=4)=[CH:22][N:23]=3)[CH:18]=[CH:19][N:20]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)C.Cl>[S:34]1[CH:35]=[CH:36][C:32]([CH2:31][NH:30][C:26]2[N:25]=[C:24]([C:21]3[N:17]4[CH:18]=[CH:19][N:20]=[C:15]([NH:14][CH:11]5[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]5)[C:16]4=[N:23][CH:22]=3)[CH:29]=[CH:28][CH:27]=2)=[CH:33]1

Participants

4

Reactant 1

HCID 68226672[4-(3-{6-[(Thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 66546523HCID 66546523, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The mixture of [4-(3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester (70 mg, 0.135 mmol) in ethanol (4 mL) and concentrated HCl (4 mL) was stirred at room temperature for 15 h. The reaction mixture was then concentrated under reduced pressure to give N-(3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-yl)-cyclohexane-1,4-diamine; hydrochloride. (Yield 83 mg). 1HNMR (300 MHz, CD3OD): δ 8.06 (s, 1H), 7.94 (d, 1H, J=5.4 Hz), 7.87 (t, 1H, J=8.7 Hz), 7.39-7.34 (m, 2H), 7.16-7.03 (m, 4H), 4.62 (s, 2H), 3.98 (brs, 1H), 3.14 (brs, 1H), 2.14-2.09 (brs, 4H), 1.70-1.60 (m, 4H). LC-MS: [M+H]+ 420.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a2b125964e34f6ab661b44d8f4183e6
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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