Dimethylformamide → HCID 178482419, compound

HRID 1671766Notes

Reaction equation

HRID 1671766 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.[N:25]1([C:32]2[N:37]=[C:36]([NH:38][CH3:39])[N:35]=[C:34]([NH:40][C@@H:41]3[CH2:46][CH2:45][C@H:44]([C:47](O)=[O:48])[CH2:43][CH2:42]3)[N:33]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CCN([CH:56]([CH3:58])C)C(C)C.[F:59][C:60]([F:70])([F:69])C1C=CC=CC=1CN.CN(C=[O:75])C>CCOC(C)=O>[N:25]1([C:32]2[N:37]=[C:36]([NH:38][CH3:39])[N:35]=[C:34]([NH:40][C@@H:41]3[CH2:46][CH2:45][C@H:44]([C:47]([NH:15][CH2:14][C:13]4[CH:12]=[CH:11][CH:10]=[CH:58][C:56]=4[O:75][C:60]([F:70])([F:69])[F:59])=[O:48])[CH2:43][CH2:42]3)[N:33]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]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 178482423HCID 178482423, compound

Product 1

HCID 178482419HCID 178482419, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HATU (10.8 mg, 0.028 mmol, 1.1 equivalents) in DMF (0.2 ml) was added to the solution of cis-4-(4-(azepan-1-yl)-6-(methylamino)-1,3,5-triazin-2-ylamino) cyclohexanecarboxylic acid (8.96 mg, 0.026 mmol, 1 equivalent) in DMF (1 ml), followed by adding DIEA (11.2 μL, 0.064 mmol, 2.5 equivalents). 2-(trifluoromethyl)-benzenemethanamine (5.9 mg, 0.031 mmol, 1.2 equivalents) in DMF (0.1 ml) was added. The reaction solution was stirred at room temperature for 2 hours. LC-MS showed the reaction had 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 final product (˜7.7 mg, 57%). MS (ES+): m/e 522.4 [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-83f3cede37154860b6c82061e231f32a
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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