Sodium borohydride → 2-[4-Hydroxymethyl-1'-methyl-5'-(5-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylamino)-6'-oxo-1',6'-dihydro-[3,3']bipyridinyl-5-yl]-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one

HRID 592683Notes

Reaction equation

HRID 592683 reaction equation
[CH3:1][C:2]1([CH3:42])[CH2:13][C:12]2[CH:11]=[C:10]3[N:5]([CH2:6][CH2:7][N:8]([C:15]4[CH:16]=[N:17][CH:18]=[C:19]([C:23]5[CH:28]=[C:27]([NH:29][C:30]6[CH:39]=[C:33]7[CH2:34][N:35]([CH3:38])[CH2:36][CH2:37][N:32]7[N:31]=6)[C:26](=[O:40])[N:25]([CH3:41])[CH:24]=5)[C:20]=4[CH:21]=[O:22])[C:9]3=[O:14])[C:4]=2[CH2:3]1.[BH4-].[Na+]>CO>[OH:22][CH2:21][C:20]1[C:15]([N:8]2[CH2:7][CH2:6][N:5]3[C:4]4[CH2:3][C:2]([CH3:1])([CH3:42])[CH2:13][C:12]=4[CH:11]=[C:10]3[C:9]2=[O:14])=[CH:16][N:17]=[CH:18][C:19]=1[C:23]1[CH:28]=[C:27]([NH:29][C:30]2[CH:39]=[C:33]3[CH2:34][N:35]([CH3:38])[CH2:36][CH2:37][N:32]3[N:31]=2)[C:26](=[O:40])[N:25]([CH3:41])[CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866842653-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-5-[1-methyl-5-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]pyridine-4-carbaldehyde

Product 1

HCID 865672592-[4-Hydroxymethyl-1'-methyl-5'-(5-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylamino)-6'-oxo-1',6'-dihydro-[3,3']bipyridinyl-5-yl]-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-oneYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 150a (170 mg, 0.30 mmol) in methanol (10 mL) was added sodium borohydride (68 mg, 1.8 mmol) at 0° C. The mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was quenched with water (2 mL) and concentrated. The residue was purified with reverse-phase prep-HPLC to afford 150 (42 mg, 25%) as a pale yellow solid. MS-ESI: [M+H]+ 569. 1H NMR (500 MHz, CDCl3) δ 8.63 (s, 1H), 8.48 (s, 1H), 7.95 (d, J=2.0 Hz, 1H), 7.40 (s, 1H), 7.32 (d, J=2.5 Hz, 1H), 6.82 (s, 1H), 5.67 (s, 1H), 4.63-4.55 (m, 2H), 4.37-4.35 (m 1H), 4.22-4.18 (m, 3H), 4.05-3.97 (m, 3H), 3.69 (s, 3H), 3.59-3.57 (m, 2H), 2.86 (t, J=6.0 Hz, 2H), 2.56 (s, 2H), 2.50 (s, 2H), 2.46 (s, 3H), 1.26 (s, 6H).

Workup

  1. customThen the reaction mixture was quenched with water (2 mL)
  2. concentrationconcentrated
  3. customThe residue was purified with reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-5db99b57244e408ba699e34753e969b8
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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