Pyrrolidine → HCID 66686506, compound

HRID 337165Notes

Reaction equation

HRID 337165 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([NH:18][C:19](=[O:47])[C:20]2[CH:25]=[C:24]([N:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:34]([CH3:37])[CH:35]=O)[C:27]3=[O:44])[C:23]([CH3:45])=[C:22]([F:46])[CH:21]=2)[CH2:17][CH2:16]1.[NH:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:15]1([NH:18][C:19](=[O:47])[C:20]2[CH:25]=[C:24]([N:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@@H:34]([CH3:37])[CH2:35][N:48]4[CH2:52][CH2:51][CH2:50][CH2:49]4)[C:27]3=[O:44])[C:23]([CH3:45])=[C:22]([F:46])[CH:21]=2)[CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86663259HCID 86663259, compound

Product 1

HCID 66686506HCID 66686506, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Sodium triacetoxyborohydride (0.284 g) was added to N-cyclopropyl-3-fluoro-4-methyl-5-[3-{[(1R,2R)-2-methyl-3-oxo-1-phenylpropyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide (Example 328e, 0.3 g), pyrrolidine (0.221 mL) and Hunig's Base (0.467 mL) in DCM (15 mL). The resulting suspension was stirred at 22° C. for 2 h. The reaction mixture was basified with satd sodium bicarbonate solution before extracting with DCM. The combined organic phases were concentrated in vacuo and the residue purified by preparative HPLC (Phenominex column using a 75-5% gradient of aqueous 0.2% ammonia in acetonitrile as eluent). The fractions containing the desired compound were evaporated to dryness to afford the title compound as a solid (0.046 g).

Workup

  1. extractionbefore extracting with DCM
  2. concentrationThe combined organic phases were concentrated in vacuo
  3. customthe residue purified by preparative HPLC (Phenominex column
  4. additionThe fractions containing the desired compound
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-d8f3a2c190814e93864b269f386c6691
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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