Water → HCID 178432772, compound

HRID 1914672Notes

Reaction equation

HRID 1914672 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][O:16]S(C(F)(F)F)(=O)=O)[CH2:11][CH2:10]1)=O)(C)(C)C.[CH3:24][C:25]1[C:29]([CH3:30])=[C:28]([CH3:31])[N:27]([CH2:32][C@H:33]2[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]2)[N:26]=1.C(N(CC)CC)C.O.C(Cl)[Cl:49]>>[Cl:49][C:10]1[CH:9]=[N:8][C:13]([CH3:14])=[C:12]([CH:11]=1)[C:15]([NH:39][C@H:36]1[CH2:35][CH2:34][C@H:33]([CH2:32][N:27]2[C:28]([CH3:31])=[C:29]([CH3:30])[C:25]([CH3:24])=[N:26]2)[CH2:38][CH2:37]1)=[O:16]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 178434053HCID 178434053, compoundHCID 178453974HCID 178453974, compound

Product 1

HCID 178432772HCID 178432772, compound

Procedure

To a suspension of 5-chloro-2-methylnicotinoyl chloride (Ex. 17 step 1) and trans-4-(3,4,5-trimethyl-pyrazol-1-ylmethyl)-cyclohexylamine (step 3) (197 mg, ca. 0.67 mmol) in dry DCM (6.5 mL) is added triethylamine (0.37 mL, 2.68 mmol). The mixture is stirred at room temp for 45 minutes. Water (20 mL) is added and the mixture is extracted with EtOAc (3×20 mL). The EtOAc extracts are combined, washed with saturated brine (20 mL), dried (MgSO4), filtered and evaporated to give a pale yellow gum. The mixture is purified by chromatography on silica gel eluting with 0-100% EtOAc to give a colourless solid which was triturated with Et2O to afford the title product. MS m/z 375.3/377.3 [M+H]+1H NMR (400 MHz, DMSO-d6) δ 8.54 (1H, d), 8.39 (1H, d), 7.79 (1H, d), 3.74 (2H, d), 3.67 (1H, m), 2.47 (3H, s), 2.10 (3H, s), 2.02 (3H, s), 1.88 (2H, m), 1.83 (3H, m), 1.70 (1H, m), 1.57 (2H, m), 1.14 (4H, m).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×20 mL)
  2. washwashed with saturated brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a pale yellow gum
  7. customThe mixture is purified by chromatography on silica gel eluting with 0-100% EtOAc
  8. customto give a colourless solid which
  9. customwas triturated with Et2O

Sources & evidence

ORD record
ord-5edd60b81ce24ed6a2361419724e5af1
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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