Hydrochloric Acid → HCID 178515455, compound

HRID 79164Notes

Reaction equation

[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][C:37]([O:39]C)=[N:38][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][C:37]([OH:39])=[N:38][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 58299569HCID 58299569, compound

Product 1

HCID 178515455HCID 178515455, compoundYield 108.2%

Conditions

Temperature: 120 °C

Procedure

A 10 mL reaction tube vessel was charged with compound 269 (56.0 mg, 103 μmol) and concentrated hydrochloric acid (2.00 mL, 103 μmol). The reaction was heated with microwave energy (300 W) at 120° C. for 1 hour, then an additional 30 minutes at 140° C. The resulting solution was filtered through a 0.45 μM filter and washed with water. The solvent was removed in vacuo, and the residue coevaporated with water (10 mL) and then methanol (2×, 10 mL) to give compound 270 as a yellow solid (48 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.63-11.91 (m, 2 H) 9.40 (br. s., 4 H) 9.19 (s, 1 H) 8.50 (d, J=8.61 Hz, 1 H) 8.04 (d, J=2.74 Hz, 1 H) 7.99 (dd, J=9.39, 2.74 Hz, 1 H) 7.51 (d, J=9.39 Hz, 1 H) 6.69-6.78 (m, 1 H) 5.35 (quin, J=8.71 Hz, 1 H) 3.37-3.51 (m, 4 H) 3.20-3.34 (m, 4 H) 2.06-2.18 (m, 2 H) 1.93-2.06 (m, 2 H) 1.66-1.82 (m, 2 H) ppm.

Workup

customA 10 mL reaction tube vessel
customan additional 30 minutes
customat 140° C
filtrationThe resulting solution was filtered through a 0.45 μM
filtrationfilter
washwashed with water
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-48c680c372534bb49921c003ebc8bcf5
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841312B2

Reaction notes

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