Acetaldehyde → HCID 11597843, compound

HRID 386191Notes

Reaction equation

HRID 386191 reaction equation
[CH:1](=O)[CH3:2].ClC(Cl)C.[C:8]1([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([C:24]4[N:25]=[C:26]([CH2:34][CH:35]5[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]5)[N:27]5[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=45)=[CH:19][CH:20]=3)[N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:38]1[CH2:39][CH2:40][CH:35]([CH2:34][C:26]2[N:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]3=[C:24]([C:18]3[CH:17]=[C:16]4[C:21]([CH:22]=[CH:23][C:14]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)=[N:15]4)=[CH:20][CH:19]=3)[N:25]=2)[CH2:36][CH2:37]1)[CH3:2]

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11517695HCID 11517695, compound

Product 1

HCID 11597843HCID 11597843, compound

Procedure

Acetaldehyde (6.76 mg, 0.15 mmol) in dichloroethane (5 mL, 2 equiv) was added to 1-(2-Phenyl-quinolin-7-yl)-3-piperidin-4-ylmethyl-imidazo[1,5-a]pyrazin-8-ylamine (100.00 mg, 0.23 mmol) and sodium triacetoxyborohydride (65.0 mg, 306.8 mmol). The reaction mixture was stirred at rt overnight. The crude product was purified by a 5 g Jones silica gel (dry loaded with silica, wetted with 100% CH2Cl2, eluted with 100% CH2Cl2→3% (7N NH3) in MeOH/CH2Cl2→6% (7N NH3) in MeOH/CH2Cl2) and afforded the desired product. 1H NMR (400 MHz, METHANOL-d) δ 8.38 (1 H, d, J=8.66), 8.25 (1 H, s), 8.08 (2 H, dd, J=1.64 Hz, J=1.08), 8.00 (2 H, m), 7.79 (1 H, dd, J=2.06, J=1.70), 7.51 (1 H, d, J=5.15), 7.44 (3 H, m), 7.00 (1 H, d, J=5.12), 3.06 (2 H, d, J=10.88), 2.97 (2 H, d, J=7.08), 2.54 (2 H, d, J=5.80), 2.18 (2 H, m), 1.98 (1H, m), 1.75 (2 H, d, J=13.12), 1.43 (2 H, m), 1.07 (3 H, t); MS (ES+): m/z 435.12/436.10 (15/5) [MH+]; HPLC: tR=1.71 min (OpenLynx, polar—5 min).

Workup

  1. customThe crude product was purified by a 5 g Jones silica gel (dry loaded with silica, wetted with 100% CH2Cl2, eluted with 100% CH2Cl2→3% (7N NH3) in MeOH/CH2Cl2→6% (7N NH3) in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2600df5bc2a84857958bf489098a52b6
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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