4-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine → (S)-4-(1-((2-(2-(1-methoxyethyl)-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine

HRID 1043637Notes

Reaction equation

HRID 1043637 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:16][CH:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:29][O:30][C@H:31]([C:33]1[NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=2[N:34]=1)[CH3:32]>>[CH3:29][O:30][C@H:31]([C:33]1[N:34]([C:2]2[N:3]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:5]3[N:11]=[C:10]([CH2:12][N:13]4[CH2:16][CH:15]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)[CH2:14]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1)[CH3:32]

Participants

3

Reactant 2

HCID 584050304-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholineHCID 67344275(S)-2-(1-methoxyethyl)-1H-benzo[d]imidazole

Product 1

HCID 58405034(S)-4-(1-((2-(2-(1-methoxyethyl)-1H-benzo[d]imidazol-1-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine

Procedure

Following General procedure D, 4-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)azetidin-3-yl)morpholine from Example 126 was reacted with (S)-2-(1-methoxyethyl)-1H-benzo[d]imidazole to give 150. 1H NMR (400 MHz, DMSO) δ 8.18 (d, J=8.6 Hz, 1H), 8.01 (dd, J=6.7, 1.8 Hz, 1H), 7.84 (d, J=8.7 Hz, 1H), 7.73 (dd, J=6.7, 2.1 Hz, 1H), 7.38-7.24 (m, 2H), 5.50 (q, J=6.4 Hz, 1H), 4.53 (br s, 4H), 3.92-3.79 (m, 6H), 3.63-3.52 (m, 4H), 3.45 (t, J=6.2 Hz, 2H), 3.09 (s, 3H), 2.97 (overlapping m, 3H), 2.25 (br s, 4H), 1.63 (d, J=6.4 Hz, 3H). LCMS: 345.3

Sources & evidence

ORD record
ord-3cf163b2cc5f47858ab43479e13ef077
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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