Hydrochloric Acid → (R)-5-(7-chlorobenzo[d]thiazol-2-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

HRID 1507525Notes

Reaction equation

HRID 1507525 reaction equation
[Cl:1][C:2]1[C:10]2[S:9][C:8]([C:11]3[C:12]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]4)=[N:13][C:14]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][C:16]=3[O:17]C)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl>>[Cl:1][C:2]1[C:10]2[S:9][C:8]([C:11]3[C:16](=[O:17])[NH:15][C:14]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[N:13][C:12]=3[NH:25][C@@H:26]3[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 89554319(3R)-tert-butyl 3-(5-(7-chlorobenzo[d]thiazol-2-yl)-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 136508778(R)-5-(7-chlorobenzo[d]thiazol-2-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

Procedure

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(7-chloro-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (40.0 mg, 0.07 mmol, 1.00 equiv) and 12 N hydrochloric acid (3.0 ml). The solid was collected by filtration and dried in vacuo to give the title compound as an off-white solid. 1H-NMR (400 MHz, DMSO-d6): ppm 1.611-1.736(m, 3H), 1.935(m, 1H), 2.621-2.819(m, 3H), 3.079-3.114(m, 1H), 3.687-3.698(m, 8H), 4.157-4.167(m, 1H), 7.306-7.325(d, J=7.6 Hz, 1H), 7.399-7.419(d, J=8.0 Hz, 1H), 7.686-7.706(d, J=8.0 Hz, 1H), 10.667-10.685(m, 1H). MS m/z [M+H]+ (ESI): 447. IRAK4 IC50=180 nM

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-44dadc3b54094452b6f37d8032947011
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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