Hydrochloric Acid → HCID 136508842, compound

HRID 1507522Notes

Reaction equation

HRID 1507522 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[C:4]=1[C:29]1[S:30][C:31]2[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=1.Cl>>[N:9]1([C:7]2[NH:8][C:3](=[O:2])[C:4]([C:29]3[S:30][C:31]4[C:37]([C:38]([F:40])([F:39])[F:41])=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)=[C:5]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)[N:6]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117686398HCID 117686398, compound

Product 1

HCID 136508842HCID 136508842, compound

Procedure

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[6-methoxy-2-(morpholin-4-yl)-5-[7-(trifluoromethyl)-1,3-benzothiazol-2-yl]pyrimidin-4-yl]amino]piperidine-1-carboxylate (40.0 mg, 0.07 mmol, 1.00 equiv) and conce. hydrochloric acid (3.0 mL). The crude product was triturated in methanol and dissolved in 5.0 ml of water. The pH value of the solution was adjusted to 11 with sodium hydroxide (1 M). The solid was collected by filtration and dried in vacuo to afford the title compound. Yield: 16.1 mg (50%). 1H-NMR (400 MHz, DMSO-d6): ppm 1.54-1.57(m, 1H), 1.63-1.73(m, 2H), 1.94(m, 1H), 2.64-2.82(m, 3H), 3.08-3.11(m, 1H), 3.69-3.70(m, 8H), 4.17-4.18(m, 1H), 7.57-7.63(m, 2H), 8.00-8.02(d, J=7.6 Hz, 1H), 10.69-10.71(m, 1H); 19F-NMR (300 MHz, DMSO-d6): ppm −61.57; MS m/z [M+H]+ (ESI): 481. IRAK4 IC50=520 nM

Workup

  1. customThe crude product was triturated in methanol
  2. dissolutiondissolved in 5.0 ml of water
  3. filtrationThe solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6d6fec9a2c5c4e788047a05d9659c43a
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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