2-Chloro-5-propylpyrimidine → HCID 57468403, compound

HRID 1676196Notes

Reaction equation

HRID 1676196 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:15][C:14]1=[O:26].Cl.CC1N(C2C=CC(S(C)(=O)=O)=CC=2)C(=O)C=C(OC2CCNCC2)C=1.Cl[C:54]1[N:59]=[CH:58][C:57]([CH2:60][CH2:61][CH3:62])=[CH:56][N:55]=1.ClC1N=CC(C2CC2)=CN=1>>[Cl:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:54]3[N:59]=[CH:58][C:57]([CH2:60][CH2:61][CH3:62])=[CH:56][N:55]=3)[CH2:22][CH2:21]2)=[CH:15][C:14]1=[O:26]

Participants

5

Reactant 4

HCID 27357842-Chloro-5-propylpyrimidineHCID 468640872-Chloro-5-cyclopropylpyrimidineHCID 67367292HCID 67367292, compoundHCID 67369718HCID 67369718, compound

Product 1

HCID 57468403HCID 57468403, compound

Procedure

Example 169 was prepared according to the procedures described in Example 168 and Example 162 substituting 1-(2-chloro-4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloride for 6-methyl-1-(4-(methylsulfonyl)phenyl)-4-(piperidin-4-yloxy)pyridin-2(1H)-one hydrochloride and 2-chloro-5-propylpyrimidine for 2-chloro-5-cyclopropylpyrimidine in Step C. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (s, 2H), 8.16 (s, 1H), 7.99 (dd, J=8.25, 2.20 Hz, 1H), 7.62 (d, J=8.25 Hz, 1H), 7.06 (d, J=7.70 Hz, 1H), 6.10 (dd, J=7.70, 2.75 Hz, 1H), 6.05 (d, J=2.75 Hz, 1H), 4.55-4.64 (m, 1H), 4.23 (dd, J=11.55, 6.05 Hz, 2H), 3.59-3.69 (m, 2H), 3.14 (s, 3H), 2.43 (t, J=7.42 Hz, 2H), 2.11 (td, J=6.32, 3.30 Hz, 2 H), 1.88 (ddd, J=8.39, 4.40, 4.26 Hz, 2H), 1.55-1.61 (m, 2H), 0.96 (t, 3H). MS (ESI) 503 (M+H).

Workup

  1. customExample 169 was prepared

Sources & evidence

ORD record
ord-d63f03647a9448dbb7aeedae6086b74d
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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