Glycolic Acid → 2-(1-((2-(2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1922940Notes

Reaction equation

HRID 1922940 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:28]1[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=[C:29]1[CH3:37])=[N:6][C:7]=2[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.NC1C=CC=CC=1NC1N=C2C(N=C(CN3CCC(C([OH:66])(C)C)CC3)N2C)=C(N2CCOCC2)N=1.C(O)(=O)CO>>[OH:66][CH2:37][C:29]1[N:28]([C:5]2[N:4]=[C:3]3[C:8]([N:9]=[C:10]([CH2:11][N:12]4[CH2:17][CH2:16][CH:15]([C:18]([OH:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]4)[N:2]3[CH3:1])=[C:7]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:6]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=1

Participants

4

Reactant 3

HCID 757Glycolic AcidHCID 498343962-(1-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-olHCID 596059592-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 596058042-(1-((2-(2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

Procedure

Following the procedures for synthesis of 157, 2-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol and glycolic acid were reacted to give 178. LCMS: M+H+=521.3. 1H-NMR (400 MHz, DMSO-d6): δ 8.17 (d, 1H), 7.68 (d, 1H), 7.31 (m, 2H), 5.28 (t, 1H), 5.08 (d, 2H), 4.27 (s, br, 4H), 4.02 (s, 1H), 3.82 (s, 3H), 3.78 (m, 4H), 3.73 (s, 2H), 2.90 (d, 2H), 2.01 (m, 2H), 1.66 (d, 2H), 1.21 (m, 3H), 1.02 (s, 6H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2d8fca9445084cb2ac59d9032a707301
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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