HCID 117683813, compound → (R)-5-(5-tert-butylbenzo[d]thiazol-2-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

HRID 1507532Notes

Reaction equation

HRID 1507532 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13]3[C:14]([NH:27][C@@H:28]4[CH2:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]4)=[N:15][C:16]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:18]=3[O:19]C)=[N:10][C:9]=2[CH:41]=1)([CH3:4])([CH3:3])[CH3:2]>Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13]3[C:18](=[O:19])[NH:17][C:16]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[N:15][C:14]=3[NH:27][C@@H:28]3[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]3)=[N:10][C:9]=2[CH:41]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 117683813HCID 117683813, compound

Product 1

HCID 136508774(R)-5-(5-tert-butylbenzo[d]thiazol-2-yl)-2-morpholino-6-(piperidin-3-ylamino)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Following the same procedure as in step 4 of Example 337 using tert-butyl (3R)-3-[[5-(5-tert-butyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (101.6 mg, 0.17 mmol, 1.00 equiv) and hydrochloric acid (10 mL, 6M). The crude product 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 0.05% TFA and CH3CN (30.0% CH3CN up to 44.0% in 7 min, up to 100.0% in 5 min, down to 30.0% in 1 min); Detector, Waters 2489 254&220 nm to afford the title compound as the corresponding FTA salt as a white solid. 1H-NMR(400 MHz, DMSO-d6): □δ ppm 1.239 (s, 1H), 1.375 (s, 9H), 1.837(d, J=9.2 Hz, 2H), 2.0(d, J=6 Hz, 1H), 2.126 (s, 1H), 2.936-3.01 (m, 2H), 3.272(d, J=11.2 Hz, 1H), 3.489(d, J=9.6 Hz, 1H), 3.706-3.726(m, 8H), 4.375(d, J=5.2 Hz, 1H), 7.349(t, J=1.6 Hz, J=8.4 Hz, 1H), 7.752(d, J=1.6 Hz, 1H), 7.849(d, J=8.4 Hz, 1H), 8.733(br, 1H), 8.866 (br, 1H), 10.768(d, J=6.8 Hz, 1H), 11.133 (s, 1H); 19F-NMR (400 MHz, DMSO-d6): δ ppm −74.25; MS m/z [M+H]+ (ESI): 469. IRAK4 IC50=1300 nM

Workup

  1. customThe crude product was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU))
  2. waitup to 100.0% in 5 min
  3. waitdown to 30.0% in 1 min)

Sources & evidence

ORD record
ord-0ac8c1eb8b8a4ccfb412fabe395b66cc
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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