Piperidin-4-ol → HCID 24947795, compound

HRID 390862Notes

Reaction equation

HRID 390862 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1>>[O:16]1[CH2:17][CH2:18][N:13]([C:4]2[C:5]3[S:10][C:9]([CH2:11][N:23]4[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]4)=[CH:8][C:6]=3[N:7]=[C:2]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)[N:3]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 79341Piperidin-4-olHCID 27343783-Pyridinylboronic acidHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 24947795HCID 24947795, compound

Procedure

2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde 10 from Example 3 (100 mg) was reacted with 4-hydroxypiperidine following the protocol in General Procedure C. One half of the crude material was then used with pyridine-3-boronic acid in General Procedure A to give 24 mg of 142 following reversed phase HPLC purification. MS (Q1) 412 (M)+.

Sources & evidence

ORD record
ord-a738fae57aa04a7aa4ff3fc116816334
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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