Hydrochloric Acid → HCID 136983868, compound

HRID 1507538Notes

Reaction equation

HRID 1507538 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[C:11]([NH:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]4)=[N:12][C:13]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:14][C:15]=3[O:16]C)=[N:7][C:6]=2[CH:38]=1.Cl.O>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[C:15](=[O:16])[NH:14][C:13]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:12][C:11]=3[NH:24][C@@H:25]3[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]3)=[N:7][C:6]=2[CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 117683816tert-butyl (3R)-3-[[5-(5-bromo-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

Product 1

HCID 136983868HCID 136983868, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(5-bromo-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (60.0 mg, 0.10 mmol, 1.00 equiv) and cone, hydrochloric acid (4.0 mL). The crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001 (SHIMADZU)): Column, SunFire Prep C18 OBD Column, 5 um, 19*150 mm,; mobile phase, water with 50 mmol NH4HCO3 and CH3CN (38.0% CH3CN up to 53.0% in 7 min, up to 100.0% in 5 min, down to 38.0% in 1 min); Detector, Waters 2489 254&220 nm to afford the title compound as a white solid. 1H-NMR(400 MHz, DMSO-d6) δ ppm 1.54-1.72(m, 3H), 1.92-1.93(m, 1H), 2.65-2.75(m, 2H), 2.86(m, 1H), 3.10-3.13(m, 1H), 3.62-3.69(m, 8H), 4.17(m, 1H), 7.37-7.39(d, J=8.4 Hz, 1H), 7.89-7.94(m, 2H), 10.74-10.75(m, 1H); MS m/z [M+H]+ (ESI): 492. IRAK4 IC50=19 nM

Workup

  1. customThe crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001 (SHIMADZU))
  2. waitdown to 38.0% in 1 min)

Sources & evidence

ORD record
ord-638bcd06e0d544e7b08c45422f58f250
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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