Sodium triacetoxyborohydride → HCID 67272397, compound

HRID 251221Notes

Reaction equation

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

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

HCID 59677563HCID 59677563, compound

Product 1

HCID 67272397HCID 67272397, compound

Procedure

Using General Procedure B: Reaction of 5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbaldehyde from above with 2-[4-(5,6,7,8-Tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione and NaBH(OAc)3 gave 2-{4-[[5-Methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-ylmethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a white foam. 1H NMR (CDCl3) δ −0.04 (s, 9H), 0.87 (t, 2H, J=8.1 Hz), 1.38-1.53 (m, 2H), 1.54-1.71 (m, 3H), 1.90-2.11 (m, 3H), 2.22 (s, 3H), 2.50-2.86 (m, 4H), 3.43 (t, 2H, J=8.3 Hz), 3.52-3.65 (m, 3H), 3.75 (d, 1H, J=13.1 Hz), 4.03-4.13 (m, 1H), 5.15 (s, 2H), 7.00 (dd, 1H, J=7.6, 4.7 Hz), 7.30 (d, 1H, J=6.2 Hz), 7.40 (s, 1H), 7.66-7.72 (m, 2H), 7.77-7.85 (m, 2H), 8.45 (dd, 1H, J=4.4, 1.5 Hz).

Sources & evidence

ORD record: ord-ad10c10725524ee4afb7fad1638a629b
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863293B2

Reaction notes

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