Dimethylformamide → HCID 178508802, compound

HRID 1671768Notes

Reaction equation

HRID 1671768 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[N:31]=[C:30]([N:32]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[N:29]=[C:28]([NH:39][C@@H:40]2[CH2:45][CH2:44][C@H:43]([C:46](O)=[O:47])[CH2:42][CH2:41]2)[N:27]=1.CCN([CH:55]([CH3:57])C)C(C)C.[F:58][C:59]([F:69])([F:68])C1C=CC=CC=1CN.CN(C=[O:74])C>CCOC(C)=O>[NH2:25][C:26]1[N:31]=[C:30]([N:32]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[N:29]=[C:28]([NH:39][C@@H:40]2[CH2:45][CH2:44][C@H:43]([C:46]([NH:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:57][C:55]=3[O:74][C:59]([F:69])([F:68])[F:58])=[O:47])[CH2:42][CH2:41]2)[N:27]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide3×HCID 764472-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508803HCID 178508803, compound

Product 1

HCID 178508802HCID 178508802, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HATU (17.4 mg, 0.046 mmol, 1.1 equivalents) in DMF (0.2 ml) was added to the solution of cis-4-(4-amino-6-(azepan-1-yl)-1,3,5-triazin-2-ylamino)cyclohexanecarboxylic acid (13.9 mg, 0.042 mmol, 1 equivalent) in DMF (1 ml), followed by adding DIEA (18.1 ul, 0.104 mmol, 2.5 equivalents). 2-(trifluoromethyl)-benzenemethanamine (9.54 mg, 0.05 mmol, 1.2 equivalents) in DMF (0.1 ml) was added. The reaction solution was stirred at room temperature for 2 hrs. LC-MS showed the reaction has completed. The reaction was diluted with EtOAc (2 ml), which was further washed with water (2×1.5 ml). The organic layer was dried and purified by RP-HPLC (Luna 5μ C8(2), 100×21 mm, 25-80% CH3CN/H2O, 0.1% TFA, 20 min) to give the desired product (12.2 mg, 58%). MS (ES+): m/e 508.4 [M+H]+.

Workup

  1. washwas further washed with water (2×1.5 ml)
  2. customThe organic layer was dried
  3. custompurified by RP-HPLC (Luna 5μ C8(2), 100×21 mm, 25-80% CH3CN/H2O, 0.1% TFA, 20 min)

Sources & evidence

ORD record
ord-9c316100cc8d47f2bba9bd8eb198000d
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

Loading…