1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58169404, compound

HRID 1484927Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:16][C:17]2[CH:21]=[C:20]([CH:22]3[CH2:24][CH2:23]3)[NH:19][N:18]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[NH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH3:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:29]([NH:28][CH2:27][CH2:26][NH:25][C:13]([C:11]1[S:12][C:8]([C:5]2[N:4]=[C:3]([NH:16][C:17]3[CH:21]=[C:20]([CH:22]4[CH2:23][CH2:24]4)[NH:19][N:18]=3)[C:2]([Br:1])=[CH:7][N:6]=2)=[CH:9][CH:10]=1)=[O:15])(=[O:31])[CH3:30]

Participants

Conditions

Temperature: 23 °C

Procedure

A 100 mL round bottomed flask was charged with 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carboxylic acid (332.5 mg, 0.82 mmol, 1 eq), N-(2-aminoethyl)acetamide (125.3 mg, 1.23 mol, 1.5 eq), EDCI (313.0 mg, 1.6 mmol, 2 eq), HOBt (221.1 mg, 1.6 mmol, 2 eq) and DIPEA (635.4 mg, 4.9 mmol, 6 equiv) in DMF (5 mL). The mixture was stirred for 12 h at 23° C. and extracted with THF (3×70 mL). The organic layers were dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (PE/EA/MeOH=1:1:0.05 as eluant) to give pale-yellow solid N-(2-acetamidoethyl)-5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-carboxamide (273.8 mg, 68.3%). LC-MS (m/z)=491.1 [M+H]+.

Workup

extractionextracted with THF (3×70 mL)
dry with materialThe organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (PE/EA/MeOH=1:1:0.05 as eluant)

Sources & evidence

ORD record: ord-294063a2a9d14d9d98b58a57b60ebb66
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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