Hydrochloric Acid → HCID 178482423, compound

HRID 1671765Notes

Reaction equation

HRID 1671765 reaction equation
[N:1]1([C:8]2[N:13]=[C:12](Cl)[N:11]=[C:10]([NH:15][C@@H:16]3[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]3)[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][NH2:26].Cl>CC#N.O>[N:1]1([C:8]2[N:13]=[C:12]([NH:26][CH3:25])[N:11]=[C:10]([NH:15][C@@H:16]3[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]3)[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 178525765HCID 178525765, compound

Product 1

HCID 178482423HCID 178482423, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To the solution of crude cis-4-(4-(azepan-1-yl)-6-chloro-1,3,5-triazin-2-ylamino)cyclohexanecarboxylic acid (0.77 mmol) in CH3CN/H2O (1/1, 20 ml) was added methylamine (0.4 ml, 6 equivalents). The reaction mixture was heated at 80° C. overnight. The reaction solution was acidified with 6N HCl. The solution was condensed to give the crude product, which was further purified by RP-HPLC (Luna 5μ C8(2), 100×21 mm, 15-60% CH3CN/H2O, 0.1% TFA, 17 min) to give the product (29 mg). MS (ES+): m/e 349.33 [M+H]+.

Workup

  1. customcondensed
  2. customto give the crude product, which
  3. customwas further purified by RP-HPLC (Luna 5μ C8(2), 100×21 mm, 15-60% CH3CN/H2O, 0.1% TFA, 17 min)

Sources & evidence

ORD record
ord-7f8074c3bc8f4ce380b8ab616caef085
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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