Triethylamine → HCID 54769959, compound

HRID 1896951Notes

Reaction equation

HRID 1896951 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:23])[CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[N:11][CH:10]=2)[CH2:2]1.[OH:24][CH:25]([CH:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1)[CH2:26][CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(CC)CC)C>ClCCl>[OH:24][CH:25]([CH:28]1[CH2:33][CH2:32][CH:31]([N:1]2[CH2:2][CH:3]([NH:5][C:6](=[O:23])[CH2:7][NH:8][C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:21])([F:20])[F:22])[CH:17]=4)[N:12]=[N:11][CH:10]=3)[CH2:4]2)[CH2:30][CH2:29]1)[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58562508HCID 58562508, compoundHCID 68003608HCID 68003608, compound

Product 1

HCID 54769959HCID 54769959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round-bottom flask, was placed a solution of N-(azetidin-3-yl)-2-(6-(trifluoromethyl)cinnolin-4-ylamino)acetamide (as prepared in the previous step, 450 mg, 1.38 mmol, 1.00 equiv) in dichloromethane (30 mL), 4-(1-hydroxypropyl)cyclohexanone (as described in Example 25, Step B) (216 mg, 1.38 mmol, 1.00 equiv), NaBH(OAc)3 (877 mg, 4.14 mmol, 3.00 equiv) and triethylamine (418 mg, 4.14 mmol, 3.00 equiv). The reaction mixture was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The crude product (500 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-5): Column, SunFire Prep C18, 5 μm, 19×100 mm; mobile phase, Water and CH3CN (30% CH3CN up to 40% in 13 min, up to 100% in 0.1 min, hold 100% in 2 min, down to 30% in 0.1 min, hold 30% in 1.4 min); Detector, UV 220&254 nm. The title compound was obtained as a light yellow solid.

Workup

  1. customInto a 100 mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product (500 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-5)
  4. waitmobile phase, Water and CH3CN (30% CH3CN up to 40% in 13 min
  5. waitup to 100% in 0.1 min
  6. customin 2 min
  7. waitdown to 30% in 0.1 min
  8. customin 1.4 min

Sources & evidence

ORD record
ord-7139ec38897a4b8f99fc076b06f2cfea
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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